# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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 
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data_230222zit7_0m
_database_code_depnum_ccdc_archive 'CCDC 2256847'
loop_
_audit_author_name
_audit_author_address
fluoro-hydroxy-methylindolinone
;Changzhou University
China
;
_audit_update_record             
;
2023-04-17 deposited with the CCDC.	2024-03-18 downloaded from the CCDC.
;
_audit_creation_date             2023-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 F N O2'
_chemical_formula_sum            'C9 H8 F N O2'
_chemical_formula_weight         181.16
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8781(12)
_cell_length_b                   9.1314(10)
_cell_length_c                   16.6641(18)
_cell_angle_alpha                90
_cell_angle_beta                 90.030(2)
_cell_angle_gamma                90
_cell_volume                     1655.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2917
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.717
_cell_measurement_theta_min      2.445
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0900 before and 0.0322 after correction.
The Ratio of minimum to maximum transmission is 0.9048.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             752
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9757
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.617
_diffrn_reflns_theta_min         1.872
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2200
_reflns_number_total             3770
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.107(8)
_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   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.003
_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)+(0.1080P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1887
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
1.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00C), C00I(H00D,H00E,H00F)
1.c Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_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
F001 F 0.80077(15) 1.13260(15) 0.40166(10) 0.0791(5) Uani 1 1 d . . . . .
F002 F 0.69957(16) 0.63269(15) 0.40167(10) 0.0793(5) Uani 1 1 d . . . . .
O003 O 0.83421(15) 0.46117(19) 0.41138(11) 0.0624(5) Uani 1 1 d . . . . .
H003 H 0.849447 0.373816 0.405786 0.094 Uiso 1 1 calc R U . . .
O004 O 0.66560(15) 0.96073(18) 0.41158(11) 0.0622(5) Uani 1 1 d . . . . .
H004 H 0.646788 0.877557 0.397659 0.093 Uiso 1 1 calc R U . . .
O005 O 0.86697(19) 0.9130(2) 0.52277(9) 0.0760(6) Uani 1 1 d . . . . .
O006 O 0.63262(19) 0.4127(2) 0.52292(9) 0.0760(6) Uani 1 1 d . . . . .
N007 N 0.94660(16) 0.8230(2) 0.40502(9) 0.0484(5) Uani 1 1 d . . . . .
N008 N 0.55352(16) 0.3230(2) 0.40511(9) 0.0480(5) Uani 1 1 d . . . . .
C009 C 0.58204(19) 0.3369(2) 0.32265(11) 0.0463(5) Uani 1 1 d . . . . .
C00A C 0.91795(19) 0.8370(2) 0.32277(11) 0.0462(5) Uani 1 1 d . . . . .
C00B C 0.6298(2) 0.4036(2) 0.45054(12) 0.0510(6) Uani 1 1 d . . . . .
C00C C 0.8699(2) 0.9045(2) 0.45036(12) 0.0512(6) Uani 1 1 d . . . . .
C00D C 0.6787(2) 0.4326(2) 0.31222(13) 0.0519(6) Uani 1 1 d . . . . .
C00E C 0.8210(2) 0.9327(2) 0.31198(13) 0.0515(6) Uani 1 1 d . . . . .
C00F C 0.7849(2) 0.9868(2) 0.39226(14) 0.0550(6) Uani 1 1 d . . . . .
C00G C 0.7156(2) 0.4866(2) 0.39198(14) 0.0547(6) Uani 1 1 d . . . . .
C00H C 1.0397(2) 0.7276(3) 0.43756(16) 0.0650(7) Uani 1 1 d . . . . .
H00A H 1.024445 0.628976 0.420317 0.097 Uiso 1 1 calc R U . . .
H00B H 1.037490 0.731975 0.495102 0.097 Uiso 1 1 calc R U . . .
H00C H 1.119056 0.758452 0.418943 0.097 Uiso 1 1 calc R U . . .
C00I C 0.4606(2) 0.2272(3) 0.43762(16) 0.0655(7) Uani 1 1 d . . . . .
H00D H 0.380732 0.262119 0.422393 0.098 Uiso 1 1 calc R U . . .
H00E H 0.467000 0.225607 0.495076 0.098 Uiso 1 1 calc R U . . .
H00F H 0.472347 0.129962 0.417032 0.098 Uiso 1 1 calc R U . . .
C00J C 0.5263(3) 0.2684(3) 0.25922(15) 0.0652(7) Uani 1 1 d . . . . .
H00J H 0.460547 0.204840 0.266853 0.078 Uiso 1 1 calc R U . . .
C00K C 0.9741(3) 0.7681(3) 0.25918(15) 0.0666(7) Uani 1 1 d . . . . .
H00K H 1.039796 0.704490 0.266729 0.080 Uiso 1 1 calc R U . . .
C00L C 0.7227(3) 0.4605(3) 0.23589(16) 0.0728(8) Uani 1 1 d . . . . .
H00L H 0.787858 0.524804 0.228089 0.087 Uiso 1 1 calc R U . . .
C00M C 0.7772(3) 0.9609(3) 0.23614(16) 0.0730(8) Uani 1 1 d . . . . .
H00M H 0.712193 1.025559 0.228496 0.088 Uiso 1 1 calc R U . . .
C00N C 0.6684(3) 0.3915(4) 0.17184(15) 0.0818(10) Uani 1 1 d . . . . .
H00N H 0.697285 0.408650 0.120185 0.098 Uiso 1 1 calc R U . . .
C00O C 0.8311(3) 0.8917(4) 0.17164(15) 0.0815(9) Uani 1 1 d . . . . .
H00O H 0.801699 0.908526 0.120039 0.098 Uiso 1 1 calc R U . . .
C00P C 0.5717(3) 0.2972(4) 0.18353(15) 0.0789(9) Uani 1 1 d . . . . .
H00P H 0.535828 0.251817 0.139381 0.095 Uiso 1 1 calc R U . . .
C00Q C 0.9282(3) 0.7979(4) 0.18345(15) 0.0820(9) Uani 1 1 d . . . . .
H00Q H 0.964207 0.753114 0.139202 0.098 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
F001 C00F 1.352(3) . ?
F002 C00G 1.355(3) . ?
O003 H003 0.8200 . ?
O003 C00G 1.350(3) . ?
O004 H004 0.8200 . ?
O004 C00F 1.358(3) . ?
O005 C00C 1.210(2) . ?
O006 C00B 1.209(2) . ?
N007 C00A 1.411(2) . ?
N007 C00C 1.349(3) . ?
N007 C00H 1.441(3) . ?
N008 C009 1.415(2) . ?
N008 C00B 1.342(3) . ?
N008 C00I 1.442(3) . ?
C009 C00D 1.378(3) . ?
C009 C00J 1.369(3) . ?
C00A C00E 1.381(3) . ?
C00A C00K 1.375(3) . ?
C00B C00G 1.549(3) . ?
C00C C00F 1.535(3) . ?
C00D C00G 1.473(3) . ?
C00D C00L 1.383(3) . ?
C00E C00F 1.479(3) . ?
C00E C00M 1.375(3) . ?
C00H H00A 0.9600 . ?
C00H H00B 0.9600 . ?
C00H H00C 0.9600 . ?
C00I H00D 0.9600 . ?
C00I H00E 0.9600 . ?
C00I H00F 0.9600 . ?
C00J H00J 0.9300 . ?
C00J C00P 1.380(4) . ?
C00K H00K 0.9300 . ?
C00K C00Q 1.384(4) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.373(5) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.378(5) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.373(5) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.374(5) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 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
C00G O003 H003 109.5 . . ?
C00F O004 H004 109.5 . . ?
C00A N007 C00H 125.11(18) . . ?
C00C N007 C00A 110.94(18) . . ?
C00C N007 C00H 123.83(19) . . ?
C009 N008 C00I 124.99(19) . . ?
C00B N008 C009 111.28(17) . . ?
C00B N008 C00I 123.60(19) . . ?
C00D C009 N008 110.31(18) . . ?
C00J C009 N008 127.7(2) . . ?
C00J C009 C00D 122.0(2) . . ?
C00E C00A N007 110.61(17) . . ?
C00K C00A N007 127.5(2) . . ?
C00K C00A C00E 121.9(2) . . ?
O006 C00B N008 128.0(2) . . ?
O006 C00B C00G 125.4(2) . . ?
N008 C00B C00G 106.59(17) . . ?
O005 C00C N007 127.7(2) . . ?
O005 C00C C00F 125.5(2) . . ?
N007 C00C C00F 106.81(18) . . ?
C009 C00D C00G 107.82(18) . . ?
C009 C00D C00L 119.8(2) . . ?
C00L C00D C00G 132.4(2) . . ?
C00A C00E C00F 107.25(18) . . ?
C00M C00E C00A 120.2(2) . . ?
C00M C00E C00F 132.6(2) . . ?
F001 C00F O004 105.47(18) . . ?
F001 C00F C00C 109.4(2) . . ?
F001 C00F C00E 113.53(18) . . ?
O004 C00F C00C 109.90(18) . . ?
O004 C00F C00E 114.2(2) . . ?
C00E C00F C00C 104.30(18) . . ?
F002 C00G C00B 109.21(18) . . ?
F002 C00G C00D 113.71(19) . . ?
O003 C00G F002 105.29(19) . . ?
O003 C00G C00B 109.95(19) . . ?
O003 C00G C00D 114.72(19) . . ?
C00D C00G C00B 103.92(19) . . ?
N007 C00H H00A 109.5 . . ?
N007 C00H H00B 109.5 . . ?
N007 C00H H00C 109.5 . . ?
H00A C00H H00B 109.5 . . ?
H00A C00H H00C 109.5 . . ?
H00B C00H H00C 109.5 . . ?
N008 C00I H00D 109.5 . . ?
N008 C00I H00E 109.5 . . ?
N008 C00I H00F 109.5 . . ?
H00D C00I H00E 109.5 . . ?
H00D C00I H00F 109.5 . . ?
H00E C00I H00F 109.5 . . ?
C009 C00J H00J 121.3 . . ?
C009 C00J C00P 117.4(3) . . ?
C00P C00J H00J 121.3 . . ?
C00A C00K H00K 121.5 . . ?
C00A C00K C00Q 116.9(3) . . ?
C00Q C00K H00K 121.5 . . ?
C00D C00L H00L 120.6 . . ?
C00N C00L C00D 118.8(3) . . ?
C00N C00L H00L 120.6 . . ?
C00E C00M H00M 120.5 . . ?
C00E C00M C00O 118.9(3) . . ?
C00O C00M H00M 120.5 . . ?
C00L C00N H00N 119.8 . . ?
C00L C00N C00P 120.5(2) . . ?
C00P C00N H00N 119.8 . . ?
C00M C00O H00O 120.0 . . ?
C00Q C00O C00M 120.1(2) . . ?
C00Q C00O H00O 120.0 . . ?
C00J C00P H00P 119.2 . . ?
C00N C00P C00J 121.6(3) . . ?
C00N C00P H00P 119.2 . . ?
C00K C00Q H00Q 119.0 . . ?
C00O C00Q C00K 122.0(3) . . ?
C00O C00Q H00Q 119.0 . . ?

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
O005 C00C C00F F001 61.3(3) . . . . ?
O005 C00C C00F O004 -54.1(3) . . . . ?
O005 C00C C00F C00E -176.9(2) . . . . ?
O006 C00B C00G F002 -60.9(3) . . . . ?
O006 C00B C00G O003 54.1(3) . . . . ?
O006 C00B C00G C00D 177.4(2) . . . . ?
N007 C00A C00E C00F 0.9(2) . . . . ?
N007 C00A C00E C00M -179.2(2) . . . . ?
N007 C00A C00K C00Q 179.0(2) . . . . ?
N007 C00C C00F F001 -118.7(2) . . . . ?
N007 C00C C00F O004 125.97(19) . . . . ?
N007 C00C C00F C00E 3.1(2) . . . . ?
N008 C009 C00D C00G -0.7(2) . . . . ?
N008 C009 C00D C00L 179.09(19) . . . . ?
N008 C009 C00J C00P -178.9(2) . . . . ?
N008 C00B C00G F002 118.6(2) . . . . ?
N008 C00B C00G O003 -126.3(2) . . . . ?
N008 C00B C00G C00D -3.0(2) . . . . ?
C009 N008 C00B O006 -177.7(2) . . . . ?
C009 N008 C00B C00G 2.8(2) . . . . ?
C009 C00D C00G F002 -116.4(2) . . . . ?
C009 C00D C00G O003 122.3(2) . . . . ?
C009 C00D C00G C00B 2.2(2) . . . . ?
C009 C00D C00L C00N 0.0(4) . . . . ?
C009 C00J C00P C00N -0.3(4) . . . . ?
C00A N007 C00C O005 177.3(2) . . . . ?
C00A N007 C00C C00F -2.7(2) . . . . ?
C00A C00E C00F F001 116.6(2) . . . . ?
C00A C00E C00F O004 -122.4(2) . . . . ?
C00A C00E C00F C00C -2.4(2) . . . . ?
C00A C00E C00M C00O 0.3(4) . . . . ?
C00A C00K C00Q C00O 0.0(4) . . . . ?
C00B N008 C009 C00D -1.4(2) . . . . ?
C00B N008 C009 C00J 178.2(2) . . . . ?
C00C N007 C00A C00E 1.2(2) . . . . ?
C00C N007 C00A C00K -178.4(2) . . . . ?
C00D C009 C00J C00P 0.8(4) . . . . ?
C00D C00L C00N C00P 0.4(4) . . . . ?
C00E C00A C00K C00Q -0.6(4) . . . . ?
C00E C00M C00O C00Q -0.9(4) . . . . ?
C00F C00E C00M C00O -179.8(2) . . . . ?
C00G C00D C00L C00N 179.7(2) . . . . ?
C00H N007 C00A C00E 177.5(2) . . . . ?
C00H N007 C00A C00K -2.2(4) . . . . ?
C00H N007 C00C O005 1.0(4) . . . . ?
C00H N007 C00C C00F -179.0(2) . . . . ?
C00I N008 C009 C00D -177.3(2) . . . . ?
C00I N008 C009 C00J 2.3(4) . . . . ?
C00I N008 C00B O006 -1.7(4) . . . . ?
C00I N008 C00B C00G 178.7(2) . . . . ?
C00J C009 C00D C00G 179.6(2) . . . . ?
C00J C009 C00D C00L -0.6(3) . . . . ?
C00K C00A C00E C00F -179.4(2) . . . . ?
C00K C00A C00E C00M 0.5(3) . . . . ?
C00L C00D C00G F002 63.8(3) . . . . ?
C00L C00D C00G O003 -57.5(3) . . . . ?
C00L C00D C00G C00B -177.5(2) . . . . ?
C00L C00N C00P C00J -0.3(4) . . . . ?
C00M C00E C00F F001 -63.3(3) . . . . ?
C00M C00E C00F O004 57.7(3) . . . . ?
C00M C00E C00F C00C 177.7(2) . . . . ?
C00M C00O C00Q C00K 0.8(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_230222zit8_0m
_database_code_depnum_ccdc_archive 'CCDC 2267747'
loop_
_audit_author_name
_audit_author_address
' dibenzyl fluoroindolinone'
;Zhejiang Shuren University
China
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2024-03-18 downloaded from the CCDC.
;
_audit_creation_date             2023-04-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            1,3-dibenzyl-3-fluoroindolin-2-one
_chemical_name_systematic        1,3-dibenzyl-3-fluoroindolin-2-one
_chemical_formula_moiety         '2(C22 H18 F N O)'
_chemical_formula_sum            'C44 H36 F2 N2 O2'
_chemical_formula_weight         662.75
_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                   8.3849(14)
_cell_length_b                   9.8150(16)
_cell_length_c                   11.0999(18)
_cell_angle_alpha                94.254(3)
_cell_angle_beta                 101.852(3)
_cell_angle_gamma                101.824(2)
_cell_volume                     868.6(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3113
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.470
_cell_measurement_theta_min      2.674
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1041 before and 0.0287 after correction.
The Ratio of minimum to maximum transmission is 0.8514.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Recrystallization in DCM: n-hexance(1?3)'
_exptl_crystal_F_000             348
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5177
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         2.548
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2996
_reflns_number_total             3766
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.118(7)
_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   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.049
_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)+(0.0486P)²+0.2351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1187
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C00C(H00B,H00C), C00G(H00G,H00H)
1.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00I),
 C00I(H00J), C00J(H00K), C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O),
 C00O(H00P), C00P(H00Q)
;
_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
F001 F 0.66122(13) 0.88087(10) 0.57074(8) 0.0586(3) Uani 1 1 d . . . . .
O002 O 0.92811(13) 0.76158(13) 0.50041(11) 0.0595(3) Uani 1 1 d . . . . .
N003 N 0.68815(14) 0.60024(12) 0.40061(10) 0.0366(3) Uani 1 1 d . . . . .
C004 C 0.76251(16) 0.42781(14) 0.25819(12) 0.0345(3) Uani 1 1 d . . . . .
C005 C 0.49191(17) 0.73371(14) 0.39014(12) 0.0357(3) Uani 1 1 d . . . . .
C006 C 0.51672(16) 0.60003(14) 0.36407(11) 0.0341(3) Uani 1 1 d . . . . .
C007 C 0.79856(18) 0.29793(15) 0.23438(14) 0.0429(3) Uani 1 1 d . . . . .
H007 H 0.811592 0.241189 0.297538 0.051 Uiso 1 1 calc R U . . .
C008 C 0.74418(18) 0.91785(14) 0.25572(14) 0.0410(3) Uani 1 1 d . . . . .
C009 C 0.77922(17) 0.72947(15) 0.45490(12) 0.0402(3) Uani 1 1 d . . . . .
C00A C 0.33294(19) 0.75901(17) 0.36288(14) 0.0456(4) Uani 1 1 d . . . . .
H00A H 0.316000 0.848593 0.379410 0.055 Uiso 1 1 calc R U . . .
C00B C 0.65808(18) 0.82971(14) 0.44757(13) 0.0398(3) Uani 1 1 d . . . . .
C00C C 0.7569(2) 0.47734(16) 0.38888(13) 0.0438(3) Uani 1 1 d . . . . .
H00B H 0.690634 0.401570 0.421050 0.053 Uiso 1 1 calc R U . . .
H00C H 0.869635 0.497891 0.440042 0.053 Uiso 1 1 calc R U . . .
C00D C 0.38483(19) 0.48864(16) 0.31065(13) 0.0449(4) Uani 1 1 d . . . . .
H00D H 0.401709 0.399296 0.292788 0.054 Uiso 1 1 calc R U . . .
C00E C 0.7419(2) 0.50974(16) 0.16261(14) 0.0457(4) Uani 1 1 d . . . . .
H00E H 0.716824 0.596710 0.176801 0.055 Uiso 1 1 calc R U . . .
C00F C 0.9071(2) 0.92362(17) 0.24280(17) 0.0510(4) Uani 1 1 d . . . . .
H00F H 0.995499 0.950877 0.311955 0.061 Uiso 1 1 calc R U . . .
C00G C 0.71207(19) 0.95608(15) 0.38171(15) 0.0456(4) Uani 1 1 d . . . . .
H00G H 0.625750 1.009400 0.371862 0.055 Uiso 1 1 calc R U . . .
H00H H 0.813263 1.016005 0.433440 0.055 Uiso 1 1 calc R U . . .
C00H C 0.8153(2) 0.25209(16) 0.11800(16) 0.0517(4) Uani 1 1 d . . . . .
H00I H 0.839522 0.164901 0.103231 0.062 Uiso 1 1 calc R U . . .
C00I C 0.19965(19) 0.6481(2) 0.31046(15) 0.0520(4) Uani 1 1 d . . . . .
H00J H 0.091643 0.662877 0.292443 0.062 Uiso 1 1 calc R U . . .
C00J C 0.22554(19) 0.51596(19) 0.28471(15) 0.0533(4) Uani 1 1 d . . . . .
H00K H 0.134168 0.443004 0.249051 0.064 Uiso 1 1 calc R U . . .
C00K C 0.6161(2) 0.87800(18) 0.15082(16) 0.0524(4) Uani 1 1 d . . . . .
H00L H 0.506464 0.874768 0.157040 0.063 Uiso 1 1 calc R U . . .
C00L C 0.7961(2) 0.33492(18) 0.02387(16) 0.0560(4) Uani 1 1 d . . . . .
H00M H 0.808691 0.304518 -0.054303 0.067 Uiso 1 1 calc R U . . .
C00M C 0.7583(2) 0.46331(18) 0.04602(15) 0.0572(4) Uani 1 1 d . . . . .
H00N H 0.743649 0.519034 -0.017779 0.069 Uiso 1 1 calc R U . . .
C00N C 0.8099(3) 0.84882(18) 0.02560(18) 0.0624(5) Uani 1 1 d . . . . .
H00O H 0.831675 0.825542 -0.051229 0.075 Uiso 1 1 calc R U . . .
C00O C 0.9388(2) 0.88928(19) 0.12840(19) 0.0605(5) Uani 1 1 d . . . . .
H00P H 1.048186 0.893661 0.121108 0.073 Uiso 1 1 calc R U . . .
C00P C 0.6486(3) 0.8428(2) 0.03648(17) 0.0635(5) Uani 1 1 d . . . . .
H00Q H 0.560863 0.814973 -0.033074 0.076 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
F001 C00B 1.4142(16) . ?
O002 C009 1.2121(17) . ?
N003 C006 1.4107(17) . ?
N003 C009 1.3622(18) . ?
N003 C00C 1.4481(18) . ?
C004 C007 1.3882(19) . ?
C004 C00C 1.5086(19) . ?
C004 C00E 1.3821(19) . ?
C005 C006 1.3888(19) . ?
C005 C00A 1.382(2) . ?
C005 C00B 1.4979(19) . ?
C006 C00D 1.3816(19) . ?
C007 H007 0.9300 . ?
C007 C00H 1.380(2) . ?
C008 C00F 1.393(2) . ?
C008 C00G 1.512(2) . ?
C008 C00K 1.382(2) . ?
C009 C00B 1.547(2) . ?
C00A H00A 0.9300 . ?
C00A C00I 1.383(2) . ?
C00B C00G 1.522(2) . ?
C00C H00B 0.9700 . ?
C00C H00C 0.9700 . ?
C00D H00D 0.9300 . ?
C00D C00J 1.393(2) . ?
C00E H00E 0.9300 . ?
C00E C00M 1.383(2) . ?
C00F H00F 0.9300 . ?
C00F C00O 1.382(2) . ?
C00G H00G 0.9700 . ?
C00G H00H 0.9700 . ?
C00H H00I 0.9300 . ?
C00H C00L 1.374(2) . ?
C00I H00J 0.9300 . ?
C00I C00J 1.377(3) . ?
C00J H00K 0.9300 . ?
C00K H00L 0.9300 . ?
C00K C00P 1.386(2) . ?
C00L H00M 0.9300 . ?
C00L C00M 1.378(2) . ?
C00M H00N 0.9300 . ?
C00N H00O 0.9300 . ?
C00N C00O 1.370(3) . ?
C00N C00P 1.372(3) . ?
C00O H00P 0.9300 . ?
C00P H00Q 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
C006 N003 C00C 124.44(12) . . ?
C009 N003 C006 111.07(11) . . ?
C009 N003 C00C 124.38(12) . . ?
C007 C004 C00C 118.69(12) . . ?
C00E C004 C007 118.66(13) . . ?
C00E C004 C00C 122.56(12) . . ?
C006 C005 C00B 108.46(12) . . ?
C00A C005 C006 120.51(13) . . ?
C00A C005 C00B 131.03(13) . . ?
C005 C006 N003 110.09(11) . . ?
C00D C006 N003 128.36(13) . . ?
C00D C006 C005 121.54(13) . . ?
C004 C007 H007 119.6 . . ?
C00H C007 C004 120.71(14) . . ?
C00H C007 H007 119.6 . . ?
C00F C008 C00G 119.94(14) . . ?
C00K C008 C00F 118.05(15) . . ?
C00K C008 C00G 122.01(14) . . ?
O002 C009 N003 126.77(14) . . ?
O002 C009 C00B 125.68(13) . . ?
N003 C009 C00B 107.55(11) . . ?
C005 C00A H00A 120.7 . . ?
C005 C00A C00I 118.51(15) . . ?
C00I C00A H00A 120.7 . . ?
F001 C00B C005 109.84(11) . . ?
F001 C00B C009 107.12(11) . . ?
F001 C00B C00G 107.28(11) . . ?
C005 C00B C009 102.70(11) . . ?
C005 C00B C00G 116.97(12) . . ?
C00G C00B C009 112.54(12) . . ?
N003 C00C C004 114.61(11) . . ?
N003 C00C H00B 108.6 . . ?
N003 C00C H00C 108.6 . . ?
C004 C00C H00B 108.6 . . ?
C004 C00C H00C 108.6 . . ?
H00B C00C H00C 107.6 . . ?
C006 C00D H00D 121.4 . . ?
C006 C00D C00J 117.10(14) . . ?
C00J C00D H00D 121.4 . . ?
C004 C00E H00E 119.8 . . ?
C004 C00E C00M 120.48(14) . . ?
C00M C00E H00E 119.8 . . ?
C008 C00F H00F 119.6 . . ?
C00O C00F C008 120.73(16) . . ?
C00O C00F H00F 119.6 . . ?
C008 C00G C00B 113.66(11) . . ?
C008 C00G H00G 108.8 . . ?
C008 C00G H00H 108.8 . . ?
C00B C00G H00G 108.8 . . ?
C00B C00G H00H 108.8 . . ?
H00G C00G H00H 107.7 . . ?
C007 C00H H00I 119.9 . . ?
C00L C00H C007 120.20(14) . . ?
C00L C00H H00I 119.9 . . ?
C00A C00I H00J 119.7 . . ?
C00J C00I C00A 120.55(15) . . ?
C00J C00I H00J 119.7 . . ?
C00D C00J H00K 119.1 . . ?
C00I C00J C00D 121.77(14) . . ?
C00I C00J H00K 119.1 . . ?
C008 C00K H00L 119.5 . . ?
C008 C00K C00P 120.94(16) . . ?
C00P C00K H00L 119.5 . . ?
C00H C00L H00M 120.2 . . ?
C00H C00L C00M 119.59(15) . . ?
C00M C00L H00M 120.2 . . ?
C00E C00M H00N 119.8 . . ?
C00L C00M C00E 120.36(15) . . ?
C00L C00M H00N 119.8 . . ?
C00O C00N H00O 120.1 . . ?
C00O C00N C00P 119.73(17) . . ?
C00P C00N H00O 120.1 . . ?
C00F C00O H00P 119.8 . . ?
C00N C00O C00F 120.37(17) . . ?
C00N C00O H00P 119.8 . . ?
C00K C00P H00Q 119.9 . . ?
C00N C00P C00K 120.18(17) . . ?
C00N C00P H00Q 119.9 . . ?

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
F001 C00B C00G C008 169.95(12) . . . . ?
O002 C009 C00B F001 -61.16(18) . . . . ?
O002 C009 C00B C005 -176.84(14) . . . . ?
O002 C009 C00B C00G 56.52(19) . . . . ?
N003 C006 C00D C00J 179.12(13) . . . . ?
N003 C009 C00B F001 119.18(12) . . . . ?
N003 C009 C00B C005 3.49(14) . . . . ?
N003 C009 C00B C00G -123.15(13) . . . . ?
C004 C007 C00H C00L -0.1(2) . . . . ?
C004 C00E C00M C00L -0.3(3) . . . . ?
C005 C006 C00D C00J -0.4(2) . . . . ?
C005 C00A C00I C00J -0.8(2) . . . . ?
C005 C00B C00G C008 -66.19(17) . . . . ?
C006 N003 C009 O002 176.74(14) . . . . ?
C006 N003 C009 C00B -3.60(15) . . . . ?
C006 N003 C00C C004 73.96(17) . . . . ?
C006 C005 C00A C00I 0.7(2) . . . . ?
C006 C005 C00B F001 -115.89(12) . . . . ?
C006 C005 C00B C009 -2.18(14) . . . . ?
C006 C005 C00B C00G 121.56(13) . . . . ?
C006 C00D C00J C00I 0.3(2) . . . . ?
C007 C004 C00C N003 -168.90(12) . . . . ?
C007 C004 C00E C00M -0.5(2) . . . . ?
C007 C00H C00L C00M -0.8(3) . . . . ?
C008 C00F C00O C00N 0.0(2) . . . . ?
C008 C00K C00P C00N -0.8(3) . . . . ?
C009 N003 C006 C005 2.24(15) . . . . ?
C009 N003 C006 C00D -177.31(13) . . . . ?
C009 N003 C00C C004 -110.02(15) . . . . ?
C009 C00B C00G C008 52.37(16) . . . . ?
C00A C005 C006 N003 -179.67(12) . . . . ?
C00A C005 C006 C00D -0.1(2) . . . . ?
C00A C005 C00B F001 63.95(19) . . . . ?
C00A C005 C00B C009 177.66(14) . . . . ?
C00A C005 C00B C00G -58.6(2) . . . . ?
C00A C00I C00J C00D 0.3(2) . . . . ?
C00B C005 C006 N003 0.20(14) . . . . ?
C00B C005 C006 C00D 179.79(12) . . . . ?
C00B C005 C00A C00I -179.15(14) . . . . ?
C00C N003 C006 C005 178.72(12) . . . . ?
C00C N003 C006 C00D -0.8(2) . . . . ?
C00C N003 C009 O002 0.3(2) . . . . ?
C00C N003 C009 C00B 179.92(12) . . . . ?
C00C C004 C007 C00H -175.95(14) . . . . ?
C00C C004 C00E C00M 175.99(15) . . . . ?
C00E C004 C007 C00H 0.7(2) . . . . ?
C00E C004 C00C N003 14.6(2) . . . . ?
C00F C008 C00G C00B -98.58(16) . . . . ?
C00F C008 C00K C00P 1.0(2) . . . . ?
C00G C008 C00F C00O -179.90(14) . . . . ?
C00G C008 C00K C00P -179.68(15) . . . . ?
C00H C00L C00M C00E 0.9(3) . . . . ?
C00K C008 C00F C00O -0.5(2) . . . . ?
C00K C008 C00G C00B 82.07(18) . . . . ?
C00O C00N C00P C00K 0.3(3) . . . . ?
C00P C00N C00O C00F 0.2(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
