# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_lbb
_database_code_depnum_ccdc_archive 'CCDC 2055439'
loop_
_audit_author_name
_audit_author_address
trifluoroethylbenzofuran
;FZU
China
;
_audit_update_record             
;
2021-01-12 deposited with the CCDC.	2021-03-01 downloaded from the CCDC.
;
_audit_creation_date             2019-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H9 F3 O3'
_chemical_formula_sum            'C12 H9 F3 O3'
_chemical_formula_weight         258.19
_chemical_melting_point          ?
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'

_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      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                   4.885(3)
_cell_length_b                   10.756(6)
_cell_length_c                   11.981(6)
_cell_angle_alpha                68.193(5)
_cell_angle_beta                 81.457(6)
_cell_angle_gamma                81.934(5)
_cell_volume                     575.5(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2018
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.919
_cell_measurement_theta_min      3.515
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.8070.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.065
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4216
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.349
_diffrn_reflns_theta_min         3.208
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1526
_reflns_number_total             2408
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0620
_refine_ls_restrained_S_all      1.053
_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)+(0.0583P)²+0.4155P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1705
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.0892(4) 0.79948(19) 0.60535(17) 0.0547(5) Uani 1 1 d . . . . .
C2 C 0.3082(5) 0.8036(3) 0.5187(2) 0.0452(6) Uani 1 1 d . . . . .
C3 C 0.7585(5) 0.7717(2) 0.3644(2) 0.0434(6) Uani 1 1 d . . . . .
O4 O 1.0356(4) 0.8617(2) 0.18098(19) 0.0666(6) Uani 1 1 d . . . . .
C5 C 1.0000(6) 0.7517(3) 0.2798(3) 0.0496(7) Uani 1 1 d . . . . .
C6 C 0.4582(5) 0.6780(2) 0.5452(2) 0.0419(6) Uani 1 1 d . . . . .
C7 C 0.6883(5) 0.6627(2) 0.4661(2) 0.0449(6) Uani 1 1 d . . . . .
H7 H 0.7932 0.5801 0.4815 0.054 Uiso 1 1 calc R . . . .
O8 O 1.1473(5) 0.6484(2) 0.2959(2) 0.0756(7) Uani 1 1 d . . . . .
C9 C 0.6014(6) 0.8966(3) 0.3416(3) 0.0533(7) Uani 1 1 d . . . . .
H9 H 0.6525 0.9692 0.2729 0.064 Uiso 1 1 calc R . . . .
C10 C 0.3735(6) 0.9138(3) 0.4187(3) 0.0584(8) Uani 1 1 d . . . . .
H10 H 0.2684 0.9963 0.4037 0.070 Uiso 1 1 calc R . . . .
C11 C 0.3198(6) 0.5930(3) 0.6557(2) 0.0496(7) Uani 1 1 d . . . . .
H11 H 0.3711 0.5027 0.6976 0.060 Uiso 1 1 calc R . . . .
F12 F -0.2554(5) 0.6565(3) 0.98084(19) 0.1058(8) Uani 1 1 d . . . . .
C13 C 0.1030(6) 0.6681(3) 0.6871(2) 0.0496(7) Uani 1 1 d . . . . .
C14 C 1.2703(7) 0.8523(4) 0.0945(3) 0.0800(10) Uani 1 1 d . . . . .
H14A H 1.2606 0.9306 0.0222 0.120 Uiso 1 1 calc GR . . . .
H14B H 1.2664 0.7733 0.0756 0.120 Uiso 1 1 calc GR . . . .
H14C H 1.4398 0.8466 0.1285 0.120 Uiso 1 1 calc GR . . . .
F15 F 0.1658(5) 0.6650(3) 0.9193(2) 0.1250(10) Uani 1 1 d . . . . .
C16 C -0.1149(6) 0.6386(3) 0.7918(3) 0.0609(8) Uani 1 1 d . . . . .
H16A H -0.2952 0.6718 0.7620 0.073 Uiso 1 1 calc R . . . .
H16B H -0.1129 0.5419 0.8320 0.073 Uiso 1 1 calc R . . . .
F17 F -0.1206(8) 0.8292(3) 0.8409(2) 0.1516(14) Uani 1 1 d . . . . .
C18 C -0.0820(8) 0.6983(4) 0.8814(3) 0.0705(9) 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
O1 C2 1.369(3) . ?
O1 C13 1.387(3) . ?
C2 C6 1.391(3) . ?
C2 C10 1.371(4) . ?
C3 C5 1.484(4) . ?
C3 C7 1.380(4) . ?
C3 C9 1.403(3) . ?
O4 C5 1.337(3) . ?
O4 C14 1.446(4) . ?
C5 O8 1.203(3) . ?
C6 C7 1.392(4) . ?
C6 C11 1.434(4) . ?
C9 C10 1.375(4) . ?
C11 C13 1.336(4) . ?
F12 C18 1.322(4) . ?
C13 C16 1.487(4) . ?
F15 C18 1.311(4) . ?
C16 C18 1.477(5) . ?
F17 C18 1.304(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
C2 O1 C13 105.7(2) . . ?
O1 C2 C6 110.3(2) . . ?
O1 C2 C10 125.9(2) . . ?
C10 C2 C6 123.8(2) . . ?
C7 C3 C5 118.0(2) . . ?
C7 C3 C9 120.5(2) . . ?
C9 C3 C5 121.5(3) . . ?
C5 O4 C14 116.2(2) . . ?
O4 C5 C3 112.4(2) . . ?
O8 C5 C3 124.7(3) . . ?
O8 C5 O4 122.9(3) . . ?
C2 C6 C7 118.4(2) . . ?
C2 C6 C11 105.6(2) . . ?
C7 C6 C11 136.0(2) . . ?
C3 C7 C6 119.1(2) . . ?
C10 C9 C3 121.3(3) . . ?
C2 C10 C9 116.9(2) . . ?
C13 C11 C6 106.9(2) . . ?
O1 C13 C16 115.8(2) . . ?
C11 C13 O1 111.6(2) . . ?
C11 C13 C16 132.6(3) . . ?
C18 C16 C13 114.2(3) . . ?
F12 C18 C16 113.1(3) . . ?
F15 C18 F12 104.5(3) . . ?
F15 C18 C16 111.9(3) . . ?
F17 C18 F12 106.0(3) . . ?
F17 C18 F15 107.1(4) . . ?
F17 C18 C16 113.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
