# 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_r20210507a
_database_code_depnum_ccdc_archive 'CCDC 2084177'
loop_
_audit_author_name
_audit_author_address
'Wei-Qiang Chen'
;Harbin Institute of Technology
China
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;
_audit_creation_date             2021-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 F2 N O3'
_chemical_formula_sum            'C15 H11 F2 N O3'
_chemical_formula_weight         291.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.1636(2)
_cell_length_b                   17.4283(6)
_cell_length_c                   14.1357(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.475(4)
_cell_angle_gamma                90
_cell_volume                     1266.31(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7464
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.7430
_cell_measurement_theta_min      1.9010
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15726
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.840
_diffrn_reflns_theta_min         1.860
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0285464000
_diffrn_orient_matrix_UB_12      -0.0369658000
_diffrn_orient_matrix_UB_13      0.0192548000
_diffrn_orient_matrix_UB_21      0.0153331000
_diffrn_orient_matrix_UB_22      0.0159237000
_diffrn_orient_matrix_UB_23      0.0463524000
_diffrn_orient_matrix_UB_31      -0.1342088000
_diffrn_orient_matrix_UB_32      -0.0060481000
_diffrn_orient_matrix_UB_33      0.0043833000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3293
_reflns_number_total             4361
_reflns_odcompleteness_completeness 99.78
_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         0.433
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.039
_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)+(0.0597P)²+0.5522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1444
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F1 F 0.74383(16) 0.62059(5) 0.40591(6) 0.0220(2) Uani 1 1 d . . . . .
F2 F 0.41462(18) 0.69260(4) 0.35221(6) 0.0226(2) Uani 1 1 d . . . . .
O1 O 0.0113(2) 0.59387(6) 0.62557(8) 0.0237(2) Uani 1 1 d . . . . .
H1 H 0.027339 0.563632 0.580222 0.036 Uiso 1 1 calc GR . . . .
O2 O 0.2353(2) 0.54081(5) 0.47755(7) 0.0206(2) Uani 1 1 d . . . . .
O3 O 0.16838(19) 0.56330(6) 0.27118(7) 0.0212(2) Uani 1 1 d . . . . .
N1 N 0.5945(2) 0.52641(6) 0.26724(8) 0.0184(2) Uani 1 1 d . . . . .
H1A H 0.752994 0.533733 0.294539 0.022 Uiso 1 1 calc R . . . .
C1 C 0.1835(3) 0.65186(7) 0.62265(10) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.1885(3) 0.70602(8) 0.69585(10) 0.0243(3) Uani 1 1 d . . . . .
H2 H 0.072512 0.701094 0.743765 0.029 Uiso 1 1 calc R . . . .
C3 C 0.3613(3) 0.76654(8) 0.69876(11) 0.0240(3) Uani 1 1 d . . . . .
H3 H 0.364434 0.802577 0.749271 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5312(3) 0.77558(8) 0.62863(10) 0.0224(3) Uani 1 1 d . . . . .
H4 H 0.650108 0.817311 0.631548 0.027 Uiso 1 1 calc R . . . .
C5 C 0.5255(3) 0.72343(8) 0.55491(10) 0.0202(3) Uani 1 1 d . . . . .
H5 H 0.639822 0.729931 0.506689 0.024 Uiso 1 1 calc R . . . .
C6 C 0.3517(3) 0.66040(7) 0.55017(9) 0.0160(2) Uani 1 1 d . . . . .
C7 C 0.3454(3) 0.60291(7) 0.47450(9) 0.0155(2) Uani 1 1 d . . . . .
C8 C 0.4805(3) 0.62041(7) 0.38369(9) 0.0160(2) Uani 1 1 d . . . . .
C9 C 0.3987(3) 0.56510(7) 0.30097(9) 0.0159(2) Uani 1 1 d . . . . .
C10 C 0.5600(3) 0.47368(8) 0.18902(10) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.7336(4) 0.47681(12) 0.12032(13) 0.0393(5) Uani 1 1 d . . . . .
H11 H 0.869149 0.513861 0.124332 0.047 Uiso 1 1 calc R . . . .
C12 C 0.7066(4) 0.42476(14) 0.04518(15) 0.0473(6) Uani 1 1 d . . . . .
H12 H 0.825195 0.426412 -0.002177 0.057 Uiso 1 1 calc R . . . .
C13 C 0.5107(3) 0.37106(10) 0.03862(12) 0.0306(4) Uani 1 1 d . . . . .
H13 H 0.493109 0.336102 -0.013158 0.037 Uiso 1 1 calc R . . . .
C14 C 0.3397(4) 0.36836(9) 0.10791(12) 0.0315(4) Uani 1 1 d . . . . .
H14 H 0.204567 0.331172 0.103763 0.038 Uiso 1 1 calc R . . . .
C15 C 0.3634(3) 0.41964(8) 0.18385(12) 0.0283(3) Uani 1 1 d . . . . .
H15 H 0.245730 0.417480 0.231509 0.034 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
F1 C8 1.3660(15) . ?
F2 C8 1.3666(14) . ?
O1 H1 0.8400 . ?
O1 C1 1.3494(16) . ?
O2 C7 1.2251(15) . ?
O3 C9 1.2234(17) . ?
N1 H1A 0.8800 . ?
N1 C9 1.3406(16) . ?
N1 C10 1.4357(17) . ?
C1 C2 1.3990(18) . ?
C1 C6 1.4128(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3811(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.4160(18) . ?
C6 C7 1.4637(17) . ?
C7 C8 1.5488(18) . ?
C8 C9 1.5429(18) . ?
C10 C11 1.384(2) . ?
C10 C15 1.382(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(2) . ?
C15 H15 0.9500 . ?

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 H1 109.5 . . ?
C9 N1 H1A 118.2 . . ?
C9 N1 C10 123.60(12) . . ?
C10 N1 H1A 118.2 . . ?
O1 C1 C2 116.65(12) . . ?
O1 C1 C6 123.61(12) . . ?
C2 C1 C6 119.73(12) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.28(13) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.96(13) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.50(13) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.93(13) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.56(12) . . ?
C1 C6 C7 119.04(11) . . ?
C5 C6 C7 122.38(12) . . ?
O2 C7 C6 123.86(12) . . ?
O2 C7 C8 116.77(11) . . ?
C6 C7 C8 119.37(11) . . ?
F1 C8 F2 106.52(10) . . ?
F1 C8 C7 109.09(10) . . ?
F1 C8 C9 111.74(10) . . ?
F2 C8 C7 109.47(10) . . ?
F2 C8 C9 106.66(10) . . ?
C9 C8 C7 113.11(10) . . ?
O3 C9 N1 127.31(12) . . ?
O3 C9 C8 117.64(11) . . ?
N1 C9 C8 114.99(11) . . ?
C11 C10 N1 118.29(13) . . ?
C15 C10 N1 120.91(13) . . ?
C15 C10 C11 120.76(13) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.99(16) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.94(16) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.45(14) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.64(15) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 119.22(14) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?

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
F1 C8 C9 O3 -175.97(11) . . . . ?
F1 C8 C9 N1 1.33(15) . . . . ?
F2 C8 C9 O3 -59.94(15) . . . . ?
F2 C8 C9 N1 117.35(12) . . . . ?
O1 C1 C2 C3 179.17(14) . . . . ?
O1 C1 C6 C5 -179.63(13) . . . . ?
O1 C1 C6 C7 -1.3(2) . . . . ?
O2 C7 C8 F1 -110.94(13) . . . . ?
O2 C7 C8 F2 132.87(12) . . . . ?
O2 C7 C8 C9 14.08(17) . . . . ?
N1 C10 C11 C12 178.44(18) . . . . ?
N1 C10 C15 C14 -178.58(14) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C1 C6 C7 O2 -12.7(2) . . . . ?
C1 C6 C7 C8 166.39(12) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C2 C1 C6 C7 179.53(13) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C4 C5 C6 C7 -178.30(13) . . . . ?
C5 C6 C7 O2 165.62(13) . . . . ?
C5 C6 C7 C8 -15.33(19) . . . . ?
C6 C1 C2 C3 -1.6(2) . . . . ?
C6 C7 C8 F1 69.95(14) . . . . ?
C6 C7 C8 F2 -46.25(16) . . . . ?
C6 C7 C8 C9 -165.03(11) . . . . ?
C7 C8 C9 O3 60.45(15) . . . . ?
C7 C8 C9 N1 -122.25(12) . . . . ?
C9 N1 C10 C11 136.12(16) . . . . ?
C9 N1 C10 C15 -45.8(2) . . . . ?
C10 N1 C9 O3 -1.4(2) . . . . ?
C10 N1 C9 C8 -178.41(11) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C10 C15 C14 -0.6(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.850
_oxdiff_exptl_absorpt_empirical_full_min 0.632
