# 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_a181019a
_database_code_depnum_ccdc_archive 'CCDC 1943209'
loop_
_audit_author_name
_audit_author_address
'Xia Zhao'
;Tianjin Normal University
China
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;
_audit_creation_date             2018-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 F3 N O'
_chemical_formula_sum            'C13 H10 F3 N O'
_chemical_formula_weight         253.22
_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                   5.0942(9)
_cell_length_b                   9.6532(13)
_cell_length_c                   11.935(2)
_cell_angle_alpha                91.045(13)
_cell_angle_beta                 91.275(14)
_cell_angle_gamma                101.201(13)
_cell_volume                     575.46(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1111
_cell_measurement_temperature    293.6(3)
_cell_measurement_theta_max      26.3190
_cell_measurement_theta_min      2.1880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3660
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         1.707
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.6(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  12.00   1.00   17.16    --  -11.24 -57.00  60.00   94
  2  ω    -76.00  16.00   1.00   17.16    --  -11.24 -77.00 -60.00   92
  3  ω    -38.00  56.00   1.00   17.16    --  -11.24  57.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1167167000
_diffrn_orient_matrix_UB_12      -0.0115745000
_diffrn_orient_matrix_UB_13      0.0325619000
_diffrn_orient_matrix_UB_21      -0.0035331000
_diffrn_orient_matrix_UB_22      0.0730267000
_diffrn_orient_matrix_UB_23      -0.0016864000
_diffrn_orient_matrix_UB_31      -0.0807820000
_diffrn_orient_matrix_UB_32      -0.0121172000
_diffrn_orient_matrix_UB_33      -0.0497212000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                875
_reflns_number_total             2014
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.018(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2014
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1682
_refine_ls_R_factor_gt           0.0938
_refine_ls_restrained_S_all      1.005
_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)+(0.1250P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2251
_refine_ls_wR_factor_ref         0.2822
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C9(H9), C4(H4), C7(H7), C5(H5), C6(H6)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
F3 F 0.4378(6) 0.4301(4) 0.3794(3) 0.0960(13) Uani 1 1 d . . . . .
O1 O 1.0261(8) 0.4356(4) 0.1208(3) 0.0739(12) Uani 1 1 d . . . . .
H1 H 1.0347 0.4175 0.1875 0.111 Uiso 1 1 calc GR . . . .
F1 F 0.6178(7) 0.3010(4) 0.2723(3) 0.1038(14) Uani 1 1 d . . . . .
F2 F 0.7736(8) 0.3494(4) 0.4385(3) 0.1175(16) Uani 1 1 d . . . . .
N1 N 0.8670(9) 0.5379(5) 0.1062(4) 0.0633(13) Uani 1 1 d . . . . .
C3 C 0.3752(9) 0.8587(5) 0.2735(4) 0.0508(13) Uani 1 1 d . . . . .
C1 C 0.6137(9) 0.6899(5) 0.1900(4) 0.0483(12) Uani 1 1 d . . . . .
C2 C 0.5287(9) 0.7521(5) 0.2823(4) 0.0476(12) Uani 1 1 d . . . . .
H2 H 0.5731 0.7235 0.3530 0.057 Uiso 1 1 calc R . . . .
C8 C 0.3026(9) 0.9003(5) 0.1658(4) 0.0525(13) Uani 1 1 d . . . . .
C11 C 0.7817(9) 0.5810(5) 0.1994(4) 0.0490(12) Uani 1 1 d . . . . .
C12 C 0.8582(9) 0.5283(5) 0.3116(4) 0.0565(14) Uani 1 1 d . . . . .
H12A H 1.0351 0.5058 0.3068 0.068 Uiso 1 1 calc R . . . .
H12B H 0.8687 0.6040 0.3671 0.068 Uiso 1 1 calc R . . . .
C10 C 0.5326(10) 0.7295(5) 0.0824(4) 0.0578(14) Uani 1 1 d . . . . .
H10 H 0.5812 0.6844 0.0188 0.069 Uiso 1 1 calc R . . . .
C9 C 0.3859(11) 0.8316(6) 0.0705(4) 0.0670(16) Uani 1 1 d . . . . .
H9 H 0.3392 0.8570 -0.0010 0.080 Uiso 1 1 calc R . . . .
C13 C 0.6743(11) 0.4043(6) 0.3503(5) 0.0652(15) Uani 1 1 d . . . . .
C4 C 0.2891(11) 0.9251(6) 0.3685(4) 0.0657(15) Uani 1 1 d . . . . .
H4 H 0.3311 0.8971 0.4397 0.079 Uiso 1 1 calc R . . . .
C7 C 0.1530(11) 1.0075(6) 0.1562(5) 0.0694(16) Uani 1 1 d . . . . .
H7 H 0.1065 1.0367 0.0860 0.083 Uiso 1 1 calc R . . . .
C5 C 0.1467(12) 1.0287(6) 0.3577(5) 0.0784(18) Uani 1 1 d . . . . .
H5 H 0.0963 1.0729 0.4214 0.094 Uiso 1 1 calc R . . . .
C6 C 0.0753(11) 1.0696(6) 0.2527(5) 0.0733(17) Uani 1 1 d . . . . .
H6 H -0.0262 1.1396 0.2465 0.088 Uiso 1 1 calc R . . . .


_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
F3 C13 1.329(6) . ?
O1 H1 0.8200 . ?
O1 N1 1.405(5) . ?
F1 C13 1.337(6) . ?
F2 C13 1.321(6) . ?
N1 C11 1.293(6) . ?
C3 C2 1.412(6) . ?
C3 C8 1.417(7) . ?
C3 C4 1.412(7) . ?
C1 C2 1.364(6) . ?
C1 C11 1.484(7) . ?
C1 C10 1.422(6) . ?
C2 H2 0.9300 . ?
C8 C9 1.420(7) . ?
C8 C7 1.404(7) . ?
C11 C12 1.511(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.458(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.355(7) . ?
C9 H9 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.351(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.389(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(7) . ?
C6 H6 0.9300 . ?

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
N1 O1 H1 109.5 . . ?
C11 N1 O1 113.2(4) . . ?
C2 C3 C8 119.1(4) . . ?
C4 C3 C2 122.4(5) . . ?
C4 C3 C8 118.5(5) . . ?
C2 C1 C11 121.8(4) . . ?
C2 C1 C10 118.4(5) . . ?
C10 C1 C11 119.8(4) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 C3 121.9(4) . . ?
C1 C2 H2 119.0 . . ?
C3 C8 C9 118.3(5) . . ?
C7 C8 C3 119.5(5) . . ?
C7 C8 C9 122.2(5) . . ?
N1 C11 C1 116.0(4) . . ?
N1 C11 C12 122.1(5) . . ?
C1 C11 C12 121.9(4) . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.6(4) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C1 C10 H10 119.3 . . ?
C9 C10 C1 121.4(5) . . ?
C9 C10 H10 119.3 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(5) . . ?
C10 C9 H9 119.6 . . ?
F3 C13 F1 104.9(5) . . ?
F3 C13 C12 113.8(5) . . ?
F1 C13 C12 112.8(5) . . ?
F2 C13 F3 106.6(5) . . ?
F2 C13 F1 106.5(5) . . ?
F2 C13 C12 111.7(5) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.1(5) . . ?
C5 C4 H4 119.4 . . ?
C8 C7 H7 120.3 . . ?
C6 C7 C8 119.4(5) . . ?
C6 C7 H7 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.9(5) . . ?
C5 C6 H6 119.6 . . ?

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
O1 N1 C11 C1 179.6(4) . . . . ?
O1 N1 C11 C12 2.1(6) . . . . ?
N1 C11 C12 C13 -91.1(6) . . . . ?
C3 C8 C9 C10 -0.4(7) . . . . ?
C3 C8 C7 C6 -1.0(7) . . . . ?
C3 C4 C5 C6 1.8(9) . . . . ?
C1 C11 C12 C13 91.5(6) . . . . ?
C1 C10 C9 C8 -1.5(8) . . . . ?
C2 C3 C8 C9 0.5(7) . . . . ?
C2 C3 C8 C7 -179.2(4) . . . . ?
C2 C3 C4 C5 178.7(5) . . . . ?
C2 C1 C11 N1 -174.8(4) . . . . ?
C2 C1 C11 C12 2.7(6) . . . . ?
C2 C1 C10 C9 3.3(7) . . . . ?
C8 C3 C2 C1 1.3(7) . . . . ?
C8 C3 C4 C5 -1.8(8) . . . . ?
C8 C7 C6 C5 1.0(8) . . . . ?
C11 C1 C2 C3 178.1(4) . . . . ?
C11 C1 C10 C9 -178.0(4) . . . . ?
C11 C12 C13 F3 -69.8(6) . . . . ?
C11 C12 C13 F1 49.5(6) . . . . ?
C11 C12 C13 F2 169.4(5) . . . . ?
C10 C1 C2 C3 -3.2(7) . . . . ?
C10 C1 C11 N1 6.6(6) . . . . ?
C10 C1 C11 C12 -175.9(4) . . . . ?
C9 C8 C7 C6 179.4(5) . . . . ?
C4 C3 C2 C1 -179.2(4) . . . . ?
C4 C3 C8 C9 -179.0(4) . . . . ?
C4 C3 C8 C7 1.3(7) . . . . ?
C4 C5 C6 C7 -1.4(9) . . . . ?
C7 C8 C9 C10 179.3(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2018-10-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.455
_oxdiff_exptl_absorpt_empirical_full_min 0.462
