# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_dd19378
_database_code_depnum_ccdc_archive 'CCDC 1965758'
loop_
_audit_author_name
_audit_author_address
'liu wei'
;wenzhou university
China
;
_audit_update_record             
;
2019-11-14 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 F3 O2'
_chemical_formula_weight         286.28

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   11.693(3)
_cell_length_b                   9.266(3)
_cell_length_c                   26.611(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2883.4(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1861
_cell_measurement_theta_min      5.815
_cell_measurement_theta_max      42.777

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5557
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12988
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.907
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2520
_reflns_number_gt                1335
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0561P)²+1.2050P] 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     SHELXL
_refine_ls_extinction_coef       0.0025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2520
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.3790(3) 0.5895(3) 0.56350(9) 0.1232(11) Uani 1 1 d . . . . .
F2 F 0.3807(2) 0.3835(3) 0.52933(8) 0.1030(9) Uani 1 1 d . . . . .
F3 F 0.5306(2) 0.4620(4) 0.56339(10) 0.1378(13) Uani 1 1 d . . . . .
O1 O 0.2675(2) 0.6159(3) 0.72657(9) 0.0750(8) Uani 1 1 d . . . . .
O2 O 0.4973(2) 0.3376(3) 0.79113(8) 0.0695(7) Uani 1 1 d . . . . .
C1 C 0.4214(3) 0.4128(3) 0.82016(12) 0.0491(8) Uani 1 1 d . . . . .
C2 C 0.4241(3) 0.3860(4) 0.87141(13) 0.0592(9) Uani 1 1 d . . . . .
H2 H 0.4764 0.3199 0.8842 0.071 Uiso 1 1 calc R U . . .
C3 C 0.3511(3) 0.4550(4) 0.90337(13) 0.0613(9) Uani 1 1 d . . . . .
C4 C 0.2746(3) 0.5569(4) 0.88360(14) 0.0682(10) Uani 1 1 d . . . . .
H4 H 0.2263 0.6075 0.9050 0.082 Uiso 1 1 calc R U . . .
C5 C 0.2707(3) 0.5821(4) 0.83312(13) 0.0600(9) Uani 1 1 d . . . . .
H5 H 0.2187 0.6489 0.8206 0.072 Uiso 1 1 calc R U . . .
C6 C 0.3433(2) 0.5096(3) 0.79968(12) 0.0493(8) Uani 1 1 d . . . . .
C7 C 0.3337(3) 0.5291(4) 0.74540(12) 0.0525(8) Uani 1 1 d . . . . .
C8 C 0.4077(3) 0.4291(3) 0.71425(11) 0.0530(8) Uani 1 1 d . . . . .
H8 H 0.3674 0.3368 0.7113 0.064 Uiso 1 1 calc R U . . .
C9 C 0.5178(3) 0.4018(4) 0.74261(13) 0.0662(10) Uani 1 1 d . . . . .
H9A H 0.5662 0.3381 0.7230 0.079 Uiso 1 1 calc R U . . .
H9B H 0.5581 0.4923 0.7470 0.079 Uiso 1 1 calc R U . . .
C10 C 0.4314(3) 0.4842(4) 0.66075(12) 0.0632(10) Uani 1 1 d . . . . .
H10A H 0.3983 0.5797 0.6573 0.076 Uiso 1 1 calc R U . . .
H10B H 0.5135 0.4938 0.6565 0.076 Uiso 1 1 calc R U . . .
C11 C 0.3852(3) 0.3889(3) 0.61851(12) 0.0529(8) Uani 1 1 d . . . . .
C12 C 0.2544(3) 0.3805(5) 0.62060(14) 0.0802(12) Uani 1 1 d . . . . .
H12A H 0.2312 0.3393 0.6521 0.120 Uiso 1 1 calc R U . . .
H12B H 0.2271 0.3212 0.5936 0.120 Uiso 1 1 calc R U . . .
H12C H 0.2229 0.4757 0.6175 0.120 Uiso 1 1 calc R U . . .
C13 C 0.4352(3) 0.2360(4) 0.62084(15) 0.0882(13) Uani 1 1 d . . . . .
H13A H 0.5171 0.2411 0.6192 0.132 Uiso 1 1 calc R U . . .
H13B H 0.4070 0.1805 0.5930 0.132 Uiso 1 1 calc R U . . .
H13C H 0.4127 0.1908 0.6518 0.132 Uiso 1 1 calc R U . . .
C14 C 0.4190(4) 0.4560(5) 0.56947(15) 0.0748(11) Uani 1 1 d . . . . .
C15 C 0.3542(4) 0.4289(5) 0.95935(14) 0.0976(15) Uani 1 1 d . . . . .
H15A H 0.2795 0.4008 0.9707 0.146 Uiso 1 1 calc R U . . .
H15B H 0.3770 0.5158 0.9762 0.146 Uiso 1 1 calc R U . . .
H15C H 0.4079 0.3535 0.9667 0.146 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 C14 1.332(4) . ?
F2 C14 1.339(4) . ?
F3 C14 1.317(4) . ?
O1 C7 1.224(4) . ?
O2 C1 1.367(4) . ?
O2 C9 1.441(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.392(4) . ?
C2 C3 1.364(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(5) . ?
C3 C15 1.510(5) . ?
C4 C5 1.364(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.460(4) . ?
C7 C8 1.515(4) . ?
C8 C9 1.514(4) . ?
C8 C10 1.538(4) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.528(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C14 1.499(5) . ?
C11 C12 1.533(5) . ?
C11 C13 1.533(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C1 O2 C9 113.9(2) . . ?
O2 C1 C2 116.8(3) . . ?
O2 C1 C6 122.2(3) . . ?
C2 C1 C6 121.0(3) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 C15 121.7(3) . . ?
C4 C3 C15 119.5(3) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.2(3) . . ?
C1 C6 C7 121.2(3) . . ?
C5 C6 C7 121.5(3) . . ?
O1 C7 C6 122.3(3) . . ?
O1 C7 C8 122.6(3) . . ?
C6 C7 C8 115.0(3) . . ?
C9 C8 C7 108.4(3) . . ?
C9 C8 C10 111.3(3) . . ?
C7 C8 C10 114.0(3) . . ?
C9 C8 H8 107.6 . . ?
C7 C8 H8 107.6 . . ?
C10 C8 H8 107.6 . . ?
O2 C9 C8 112.0(3) . . ?
O2 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
O2 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C8 115.1(3) . . ?
C11 C10 H10A 108.5 . . ?
C8 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C8 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C14 C11 C10 107.9(3) . . ?
C14 C11 C12 108.4(3) . . ?
C10 C11 C12 110.8(3) . . ?
C14 C11 C13 108.5(3) . . ?
C10 C11 C13 111.7(3) . . ?
C12 C11 C13 109.4(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
F3 C14 F1 107.1(4) . . ?
F3 C14 F2 104.8(3) . . ?
F1 C14 F2 104.7(3) . . ?
F3 C14 C11 112.7(3) . . ?
F1 C14 C11 113.4(3) . . ?
F2 C14 C11 113.5(3) . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C9 O2 C1 C2 -160.3(3) . . . . ?
C9 O2 C1 C6 21.0(4) . . . . ?
O2 C1 C2 C3 -179.5(3) . . . . ?
C6 C1 C2 C3 -0.8(5) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C1 C2 C3 C15 -179.0(3) . . . . ?
C2 C3 C4 C5 2.4(5) . . . . ?
C15 C3 C4 C5 179.9(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
O2 C1 C6 C5 -179.1(3) . . . . ?
C2 C1 C6 C5 2.2(5) . . . . ?
O2 C1 C6 C7 3.8(5) . . . . ?
C2 C1 C6 C7 -174.8(3) . . . . ?
C4 C5 C6 C1 -1.3(5) . . . . ?
C4 C5 C6 C7 175.7(3) . . . . ?
C1 C6 C7 O1 -178.3(3) . . . . ?
C5 C6 C7 O1 4.8(5) . . . . ?
C1 C6 C7 C8 4.5(4) . . . . ?
C5 C6 C7 C8 -172.5(3) . . . . ?
O1 C7 C8 C9 148.6(3) . . . . ?
C6 C7 C8 C9 -34.1(4) . . . . ?
O1 C7 C8 C10 24.1(4) . . . . ?
C6 C7 C8 C10 -158.7(3) . . . . ?
C1 O2 C9 C8 -53.3(4) . . . . ?
C7 C8 C9 O2 59.2(4) . . . . ?
C10 C8 C9 O2 -174.7(3) . . . . ?
C9 C8 C10 C11 119.6(3) . . . . ?
C7 C8 C10 C11 -117.5(3) . . . . ?
C8 C10 C11 C14 -178.3(3) . . . . ?
C8 C10 C11 C12 63.2(4) . . . . ?
C8 C10 C11 C13 -59.1(4) . . . . ?
C10 C11 C14 F3 62.6(4) . . . . ?
C12 C11 C14 F3 -177.3(3) . . . . ?
C13 C11 C14 F3 -58.5(4) . . . . ?
C10 C11 C14 F1 -59.2(4) . . . . ?
C12 C11 C14 F1 60.9(4) . . . . ?
C13 C11 C14 F1 179.6(3) . . . . ?
C10 C11 C14 F2 -178.5(3) . . . . ?
C12 C11 C14 F2 -58.4(4) . . . . ?
C13 C11 C14 F2 60.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O1 0.98 2.62 3.568(4) 163.9 8_655
C8 H8 O1 0.98 2.62 3.568(4) 163.9 8_655
C8 H8 O1 0.98 2.62 3.568(4) 163.9 8_655
C8 H8 O1 0.98 2.62 3.568(4) 163.9 8_655
C8 H8 O1 0.98 2.62 3.568(4) 163.9 8_655

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-4



