# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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. 
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data_211013sc1_0m
_database_code_depnum_ccdc_archive 'CCDC 2151231'
loop_
_audit_author_name
_audit_author_address
'Chao Chen'
;Zhejiang Shuren University
China
;
_audit_update_record             
;
2022-02-10 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;
_audit_creation_date             2022-02-10
_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        
3-(3-fluoro-1-methyl-2-oxoindolin-3-yl)-1-methylquinoxalin-2(1H)-one
_chemical_formula_moiety         'C18 H14 F N3 O2'
_chemical_formula_sum            'C18 H14 F N3 O2'
_chemical_formula_weight         323.32
_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                   11.3251(15)
_cell_length_b                   11.4665(15)
_cell_length_c                   11.4636(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.247(2)
_cell_angle_gamma                90
_cell_volume                     1486.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.814
_cell_measurement_theta_min      2.463
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0753 before and 0.0348 after correction.
The Ratio of minimum to maximum transmission is 0.9307.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.127
_diffrn_reflns_theta_min         2.514
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.945
_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                2473
_reflns_number_total             3425
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.057
_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)+(0.0702P)²+0.1544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1333
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00C), C00O(H00D,H00H,H00I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.24343(8) 0.81500(8) 0.26892(9) 0.0485(3) Uani 1 1 d . . . . .
O002 O 0.28210(10) 0.53220(10) 0.49307(12) 0.0496(3) Uani 1 1 d . . . . .
N003 N 0.44238(10) 0.61439(10) 0.58811(10) 0.0313(3) Uani 1 1 d . . . . .
N004 N 0.41933(11) 0.79816(10) 0.42553(11) 0.0337(3) Uani 1 1 d . . . . .
O005 O 0.29775(12) 0.57698(13) 0.19270(11) 0.0588(4) Uani 1 1 d . . . . .
N006 N 0.11673(12) 0.56462(12) 0.26881(12) 0.0424(3) Uani 1 1 d . . . . .
C007 C 0.52412(12) 0.70394(13) 0.59273(13) 0.0309(3) Uani 1 1 d . . . . .
C008 C 0.51305(12) 0.79313(12) 0.50873(13) 0.0324(3) Uani 1 1 d . . . . .
C009 C 0.34479(12) 0.71498(13) 0.42572(13) 0.0313(3) Uani 1 1 d . . . . .
C00A C 0.05622(13) 0.62376(13) 0.35412(14) 0.0350(3) Uani 1 1 d . . . . .
C00B C 0.35211(13) 0.61289(13) 0.50424(13) 0.0330(3) Uani 1 1 d . . . . .
C00C C 0.12372(13) 0.71581(13) 0.40140(14) 0.0341(3) Uani 1 1 d . . . . .
C00D C 0.23704(13) 0.71783(13) 0.34188(14) 0.0347(4) Uani 1 1 d . . . . .
C00E C 0.59614(13) 0.88247(14) 0.50941(15) 0.0397(4) Uani 1 1 d . . . . .
H00E H 0.589935 0.940922 0.453148 0.048 Uiso 1 1 calc R U . . .
C00F C 0.08506(14) 0.78396(14) 0.48963(15) 0.0398(4) Uani 1 1 d . . . . .
H00F H 0.131854 0.843953 0.521394 0.048 Uiso 1 1 calc R U . . .
C00G C 0.61732(14) 0.70645(15) 0.67801(15) 0.0410(4) Uani 1 1 d . . . . .
H00G H 0.625331 0.648035 0.734185 0.049 Uiso 1 1 calc R U . . .
C00H C 0.44874(15) 0.51913(14) 0.67418(14) 0.0405(4) Uani 1 1 d . . . . .
H00A H 0.526739 0.486059 0.677922 0.061 Uiso 1 1 calc R U . . .
H00B H 0.392014 0.460070 0.651217 0.061 Uiso 1 1 calc R U . . .
H00C H 0.431634 0.549105 0.749574 0.061 Uiso 1 1 calc R U . . .
C00I C 0.22494(15) 0.60961(15) 0.25861(15) 0.0412(4) Uani 1 1 d . . . . .
C00J C -0.05264(14) 0.60028(15) 0.39483(16) 0.0454(4) Uani 1 1 d . . . . .
H00J H -0.098489 0.538752 0.364907 0.054 Uiso 1 1 calc R U . . .
C00K C 0.69632(14) 0.79626(16) 0.67724(17) 0.0479(5) Uani 1 1 d . . . . .
H00K H 0.757981 0.798959 0.734316 0.057 Uiso 1 1 calc R U . . .
C00L C 0.68702(14) 0.88396(16) 0.59322(17) 0.0469(4) Uani 1 1 d . . . . .
H00L H 0.742673 0.943640 0.594094 0.056 Uiso 1 1 calc R U . . .
C00M C -0.09222(15) 0.67191(16) 0.48270(16) 0.0479(4) Uani 1 1 d . . . . .
H00M H -0.166788 0.658494 0.510020 0.057 Uiso 1 1 calc R U . . .
C00N C -0.02537(15) 0.76135(16) 0.53036(17) 0.0480(4) Uani 1 1 d . . . . .
H00N H -0.054054 0.806661 0.589796 0.058 Uiso 1 1 calc R U . . .
C00O C 0.07430(19) 0.46211(16) 0.20556(18) 0.0578(5) Uani 1 1 d . . . . .
H00D H 0.056405 0.401962 0.260073 0.087 Uiso 1 1 calc R U . . .
H00H H 0.134190 0.434933 0.156133 0.087 Uiso 1 1 calc R U . . .
H00I H 0.004201 0.481492 0.158554 0.087 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 C00D 1.3976(17) . ?
O002 C00B 1.2204(18) . ?
N003 C007 1.3815(18) . ?
N003 C00B 1.3634(19) . ?
N003 C00H 1.4709(19) . ?
N004 C008 1.387(2) . ?
N004 C009 1.2737(18) . ?
O005 C00I 1.209(2) . ?
N006 C00A 1.401(2) . ?
N006 C00I 1.341(2) . ?
N006 C00O 1.449(2) . ?
C007 C008 1.405(2) . ?
C007 C00G 1.398(2) . ?
C008 C00E 1.391(2) . ?
C009 C00B 1.476(2) . ?
C009 C00D 1.510(2) . ?
C00A C00C 1.395(2) . ?
C00A C00J 1.369(2) . ?
C00C C00D 1.487(2) . ?
C00C C00F 1.370(2) . ?
C00D C00I 1.567(2) . ?
C00E H00E 0.9300 . ?
C00E C00L 1.368(2) . ?
C00F H00F 0.9300 . ?
C00F C00N 1.384(2) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.365(2) . ?
C00H H00A 0.9600 . ?
C00H H00B 0.9600 . ?
C00H H00C 0.9600 . ?
C00J H00J 0.9300 . ?
C00J C00M 1.393(3) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.392(3) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.370(3) . ?
C00N H00N 0.9300 . ?
C00O H00D 0.9600 . ?
C00O H00H 0.9600 . ?
C00O H00I 0.9600 . ?

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
C007 N003 C00H 121.26(12) . . ?
C00B N003 C007 120.70(12) . . ?
C00B N003 C00H 118.03(12) . . ?
C009 N004 C008 116.68(13) . . ?
C00A N006 C00O 125.50(15) . . ?
C00I N006 C00A 111.12(13) . . ?
C00I N006 C00O 123.19(16) . . ?
N003 C007 C008 118.75(13) . . ?
N003 C007 C00G 121.33(14) . . ?
C00G C007 C008 119.92(14) . . ?
N004 C008 C007 122.43(13) . . ?
N004 C008 C00E 117.67(14) . . ?
C00E C008 C007 119.87(14) . . ?
N004 C009 C00B 125.49(13) . . ?
N004 C009 C00D 119.63(13) . . ?
C00B C009 C00D 114.87(12) . . ?
C00C C00A N006 111.01(14) . . ?
C00J C00A N006 128.93(15) . . ?
C00J C00A C00C 120.04(15) . . ?
O002 C00B N003 122.70(14) . . ?
O002 C00B C009 121.57(14) . . ?
N003 C00B C009 115.72(12) . . ?
C00A C00C C00D 107.56(13) . . ?
C00F C00C C00A 121.84(15) . . ?
C00F C00C C00D 130.55(14) . . ?
F001 C00D C009 109.32(12) . . ?
F001 C00D C00C 111.24(12) . . ?
F001 C00D C00I 105.81(12) . . ?
C009 C00D C00I 114.22(12) . . ?
C00C C00D C009 113.26(12) . . ?
C00C C00D C00I 102.66(12) . . ?
C008 C00E H00E 120.2 . . ?
C00L C00E C008 119.68(16) . . ?
C00L C00E H00E 120.2 . . ?
C00C C00F H00F 120.8 . . ?
C00C C00F C00N 118.37(16) . . ?
C00N C00F H00F 120.8 . . ?
C007 C00G H00G 120.6 . . ?
C00K C00G C007 118.71(16) . . ?
C00K C00G H00G 120.6 . . ?
N003 C00H H00A 109.5 . . ?
N003 C00H H00B 109.5 . . ?
N003 C00H H00C 109.5 . . ?
H00A C00H H00B 109.5 . . ?
H00A C00H H00C 109.5 . . ?
H00B C00H H00C 109.5 . . ?
O005 C00I N006 126.48(17) . . ?
O005 C00I C00D 125.92(15) . . ?
N006 C00I C00D 107.48(13) . . ?
C00A C00J H00J 121.2 . . ?
C00A C00J C00M 117.59(16) . . ?
C00M C00J H00J 121.2 . . ?
C00G C00K H00K 119.1 . . ?
C00G C00K C00L 121.71(16) . . ?
C00L C00K H00K 119.1 . . ?
C00E C00L C00K 120.09(15) . . ?
C00E C00L H00L 120.0 . . ?
C00K C00L H00L 120.0 . . ?
C00J C00M H00M 118.8 . . ?
C00N C00M C00J 122.44(16) . . ?
C00N C00M H00M 118.8 . . ?
C00F C00N H00N 120.2 . . ?
C00M C00N C00F 119.69(17) . . ?
C00M C00N H00N 120.2 . . ?
N006 C00O H00D 109.5 . . ?
N006 C00O H00H 109.5 . . ?
N006 C00O H00I 109.5 . . ?
H00D C00O H00H 109.5 . . ?
H00D C00O H00I 109.5 . . ?
H00H C00O H00I 109.5 . . ?

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 C00D C00I O005 63.52(19) . . . . ?
F001 C00D C00I N006 -112.80(14) . . . . ?
N003 C007 C008 N004 3.8(2) . . . . ?
N003 C007 C008 C00E -178.14(13) . . . . ?
N003 C007 C00G C00K 179.08(14) . . . . ?
N004 C008 C00E C00L 177.01(14) . . . . ?
N004 C009 C00B O002 -174.20(15) . . . . ?
N004 C009 C00B N003 5.0(2) . . . . ?
N004 C009 C00D F001 4.05(19) . . . . ?
N004 C009 C00D C00C -120.59(15) . . . . ?
N004 C009 C00D C00I 122.36(16) . . . . ?
N006 C00A C00C C00D 0.45(17) . . . . ?
N006 C00A C00C C00F -177.56(14) . . . . ?
N006 C00A C00J C00M 178.74(16) . . . . ?
C007 N003 C00B O002 175.74(14) . . . . ?
C007 N003 C00B C009 -3.45(19) . . . . ?
C007 C008 C00E C00L -1.1(2) . . . . ?
C007 C00G C00K C00L -0.8(2) . . . . ?
C008 N004 C009 C00B -2.0(2) . . . . ?
C008 N004 C009 C00D 176.78(13) . . . . ?
C008 C007 C00G C00K -0.2(2) . . . . ?
C008 C00E C00L C00K 0.1(2) . . . . ?
C009 N004 C008 C007 -2.5(2) . . . . ?
C009 N004 C008 C00E 179.40(14) . . . . ?
C009 C00D C00I O005 -56.8(2) . . . . ?
C009 C00D C00I N006 126.91(14) . . . . ?
C00A N006 C00I O005 179.84(16) . . . . ?
C00A N006 C00I C00D -3.87(17) . . . . ?
C00A C00C C00D F001 110.23(14) . . . . ?
C00A C00C C00D C009 -126.18(13) . . . . ?
C00A C00C C00D C00I -2.53(15) . . . . ?
C00A C00C C00F C00N -1.4(2) . . . . ?
C00A C00J C00M C00N -1.6(3) . . . . ?
C00B N003 C007 C008 -0.5(2) . . . . ?
C00B N003 C007 C00G -179.81(14) . . . . ?
C00B C009 C00D F001 -177.06(12) . . . . ?
C00B C009 C00D C00C 58.30(17) . . . . ?
C00B C009 C00D C00I -58.76(17) . . . . ?
C00C C00A C00J C00M 0.7(2) . . . . ?
C00C C00D C00I O005 -179.77(16) . . . . ?
C00C C00D C00I N006 3.91(15) . . . . ?
C00C C00F C00N C00M 0.5(3) . . . . ?
C00D C009 C00B O002 7.0(2) . . . . ?
C00D C009 C00B N003 -173.81(12) . . . . ?
C00D C00C C00F C00N -178.91(15) . . . . ?
C00F C00C C00D F001 -72.0(2) . . . . ?
C00F C00C C00D C009 51.6(2) . . . . ?
C00F C00C C00D C00I 175.24(16) . . . . ?
C00G C007 C008 N004 -176.87(13) . . . . ?
C00G C007 C008 C00E 1.2(2) . . . . ?
C00G C00K C00L C00E 0.8(3) . . . . ?
C00H N003 C007 C008 -179.48(13) . . . . ?
C00H N003 C007 C00G 1.2(2) . . . . ?
C00H N003 C00B O002 -5.2(2) . . . . ?
C00H N003 C00B C009 175.58(12) . . . . ?
C00I N006 C00A C00C 2.31(19) . . . . ?
C00I N006 C00A C00J -175.88(16) . . . . ?
C00J C00A C00C C00D 178.82(14) . . . . ?
C00J C00A C00C C00F 0.8(2) . . . . ?
C00J C00M C00N C00F 1.0(3) . . . . ?
C00O N006 C00A C00C 177.46(15) . . . . ?
C00O N006 C00A C00J -0.7(3) . . . . ?
C00O N006 C00I O005 4.6(3) . . . . ?
C00O N006 C00I C00D -179.15(14) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/n-hexane=1?4'
