# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_ljq1201907051
_database_code_depnum_ccdc_archive 'CCDC 1972523'
loop_
_audit_author_name
_audit_author_address
Isoxazole
;Wei Wu
China
;
_audit_update_record             
;
2019-12-17 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_audit_creation_date             2019-12-17
_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         'C10 H5 F4 N O'
_chemical_formula_sum            'C10 H5 F4 N O'
_chemical_formula_weight         231.15
_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'
N N 0.0061 0.0033 '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                   5.337(10)
_cell_length_b                   7.907(15)
_cell_length_c                   11.41(2)
_cell_angle_alpha                90.42(3)
_cell_angle_beta                 99.00(3)
_cell_angle_gamma                95.19(2)
_cell_volume                     473.6(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    753
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.461
_cell_measurement_theta_min      3.124
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1075 before and 0.0290 after correction.
The Ratio of minimum to maximum transmission is 0.8529.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2443
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         1.807
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.946
_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                1050
_reflns_number_total             1582
_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         0.292
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.065
_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)+(0.1117P)²+0.0746P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1759
_refine_ls_wR_factor_ref         0.1973
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.3688(5) 0.2219(4) 0.8948(2) 0.0545(7) Uani 1 1 d . . . . .
O3 O 0.0977(4) 0.1633(3) 0.73723(19) 0.0830(8) Uani 1 1 d . . . . .
C3 C 0.4725(5) 0.2366(3) 1.0206(2) 0.0536(7) Uani 1 1 d . . . . .
C4 C 0.4877(6) 0.2687(4) 0.7966(3) 0.0593(8) Uani 1 1 d . . . . .
N1 N 0.1367(5) 0.1602(4) 0.8605(2) 0.0811(9) Uani 1 1 d . . . . .
F1 F 1.0076(4) 0.4443(3) 1.2111(2) 0.1093(9) Uani 1 1 d . . . . .
C7 C 0.3443(6) 0.1585(4) 1.1038(3) 0.0653(9) Uani 1 1 d . . . . .
C8 C 0.7004(6) 0.3322(4) 1.0574(3) 0.0621(8) Uani 1 1 d . . . . .
C9 C 0.7895(6) 0.3468(4) 1.1756(3) 0.0703(9) Uani 1 1 d . . . . .
C10 C 0.3129(6) 0.2283(4) 0.7042(3) 0.0626(8) Uani 1 1 d . . . . .
F2 F 0.5313(5) 0.3024(5) 0.5530(2) 0.1487(13) Uani 1 1 d . . . . .
C12 C 0.4408(7) 0.1752(5) 1.2219(3) 0.0781(10) Uani 1 1 d . . . . .
C13 C 0.6656(8) 0.2693(5) 1.2588(3) 0.0772(10) Uani 1 1 d . . . . .
F4 F 0.2579(7) 0.0991(4) 0.5193(2) 0.1514(13) Uani 1 1 d . . . . .
F3 F 0.1516(7) 0.3438(5) 0.5268(2) 0.1564(13) Uani 1 1 d . . . . .
C17 C 0.3129(8) 0.2428(6) 0.5766(3) 0.0870(11) Uani 1 1 d . . . . .
H12 H 0.338(4) 0.116(3) 1.288(2) 0.038(6) Uiso 1 1 d . . . . .
H8 H 0.807(6) 0.394(4) 1.003(3) 0.074(9) Uiso 1 1 d . . . . .
H4 H 0.651(7) 0.312(5) 0.791(3) 0.089(11) Uiso 1 1 d . . . . .
H13 H 0.725(6) 0.291(4) 1.331(3) 0.074(10) Uiso 1 1 d . . . . .
H7 H 0.194(6) 0.089(4) 1.079(3) 0.071(10) Uiso 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 C3 1.455(5) . ?
C1 C4 1.408(4) . ?
C1 N1 1.289(4) . ?
O3 N1 1.390(4) . ?
O3 C10 1.326(4) . ?
C3 C7 1.374(5) . ?
C3 C8 1.377(5) . ?
C4 C10 1.311(5) . ?
F1 C9 1.341(4) . ?
C7 C12 1.366(5) . ?
C8 C9 1.359(5) . ?
C9 C13 1.359(6) . ?
C10 C17 1.461(6) . ?
F2 C17 1.286(5) . ?
C12 C13 1.359(6) . ?
F4 C17 1.294(5) . ?
F3 C17 1.296(5) . ?

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 C1 C3 129.0(3) . . ?
N1 C1 C3 120.4(2) . . ?
N1 C1 C4 110.6(3) . . ?
C10 O3 N1 107.6(2) . . ?
C7 C3 C1 120.9(3) . . ?
C7 C3 C8 119.3(3) . . ?
C8 C3 C1 119.8(3) . . ?
C10 C4 C1 104.5(3) . . ?
C1 N1 O3 106.2(2) . . ?
C12 C7 C3 120.6(4) . . ?
C9 C8 C3 118.4(3) . . ?
F1 C9 C8 118.1(3) . . ?
F1 C9 C13 119.0(3) . . ?
C13 C9 C8 122.9(4) . . ?
O3 C10 C17 116.5(3) . . ?
C4 C10 O3 111.1(3) . . ?
C4 C10 C17 132.5(3) . . ?
C13 C12 C7 120.4(3) . . ?
C12 C13 C9 118.4(4) . . ?
F2 C17 C10 112.0(3) . . ?
F2 C17 F4 106.1(4) . . ?
F2 C17 F3 105.7(4) . . ?
F4 C17 C10 113.2(3) . . ?
F4 C17 F3 106.1(4) . . ?
F3 C17 C10 113.1(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
