# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_1ver0-17761_kai199_auto
_audit_block_doi                 10.5517/ccdc.csd.cc277m37
_database_code_depnum_ccdc_archive 'CCDC 2062898'
loop_
_audit_author_name
_audit_author_address
'Anna Inyutina'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2021-02-13 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-02-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
7-fluoro-5-methyl-2-phenylbenzo[e]pyrrolo[3,4-b]azepine-1,3(2H,3aH)-dione
_chemical_formula_moiety         'C19 H13 F N2 O2'
_chemical_formula_sum            'C19 H13 F N2 O2'
_chemical_formula_weight         320.31
_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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.5776(2)
_cell_length_b                   14.3577(2)
_cell_length_c                   11.1685(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.979(3)
_cell_angle_gamma                90
_cell_volume                     1524.77(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5185
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      73.6190
_cell_measurement_theta_min      4.6290
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.789
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.561
_oxdiff_exptl_absorpt_empirical_full_max 1.960
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8152
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.778
_diffrn_reflns_theta_min         4.650
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2616
_reflns_number_total             2927
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.033
_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)+(0.0437P)²+0.3178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0853
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C19(H19), C21(H21),
 C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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
F24 F 0.19796(8) 0.96986(5) 0.66403(8) 0.0310(2) Uani 1 1 d . . . . .
O1 O 0.49139(8) 0.43127(6) 0.59993(8) 0.01751(18) Uani 1 1 d . . . . .
O2 O 0.02267(8) 0.42450(6) 0.31204(9) 0.0215(2) Uani 1 1 d . . . . .
N3 N 0.26333(10) 0.41014(7) 0.44133(10) 0.0159(2) Uani 1 1 d . . . . .
N4 N 0.34466(9) 0.56747(7) 0.69365(10) 0.0155(2) Uani 1 1 d . . . . .
C5 C 0.28350(11) 0.32056(8) 0.39529(11) 0.0164(2) Uani 1 1 d . . . . .
C6 C 0.35711(11) 0.31529(9) 0.31851(12) 0.0194(2) Uani 1 1 d . . . . .
H6 H 0.389728 0.370175 0.293501 0.023 Uiso 1 1 calc R U . . .
C7 C 0.38205(12) 0.22813(9) 0.27907(12) 0.0233(3) Uani 1 1 d . . . . .
H7 H 0.433335 0.223319 0.227608 0.028 Uiso 1 1 calc R U . . .
C8 C 0.33287(13) 0.14823(9) 0.31403(13) 0.0254(3) Uani 1 1 d . . . . .
H8 H 0.350990 0.088944 0.287067 0.030 Uiso 1 1 calc R U . . .
C9 C 0.25689(14) 0.15476(9) 0.38868(13) 0.0255(3) Uani 1 1 d . . . . .
H9 H 0.221908 0.100024 0.411537 0.031 Uiso 1 1 calc R U . . .
C10 C 0.23224(13) 0.24145(9) 0.42976(12) 0.0215(3) Uani 1 1 d . . . . .
H10 H 0.180713 0.246339 0.480995 0.026 Uiso 1 1 calc R U . . .
C11 C 0.13257(12) 0.45602(8) 0.39371(11) 0.0159(2) Uani 1 1 d . . . . .
C12 C 0.37272(11) 0.46017(8) 0.53835(11) 0.0146(2) Uani 1 1 d . . . . .
C13 C 0.31516(11) 0.55455(7) 0.55411(11) 0.0141(2) Uani 1 1 d . . . . .
H13 H 0.358874 0.605748 0.524285 0.017 Uiso 1 1 calc R U . . .
C14 C 0.16179(11) 0.54692(8) 0.46269(11) 0.0148(2) Uani 1 1 d . . . . .
C15 C 0.06812(11) 0.61447(8) 0.44275(11) 0.0161(2) Uani 1 1 d . . . . .
H15 H -0.027490 0.603154 0.383165 0.019 Uiso 1 1 calc R U . . .
C16 C 0.10590(11) 0.70495(8) 0.50833(11) 0.0156(2) Uani 1 1 d . . . . .
C17 C 0.30105(11) 0.64164(8) 0.72654(11) 0.0159(2) Uani 1 1 d . . . . .
C18 C 0.21767(11) 0.71914(8) 0.63645(11) 0.0153(2) Uani 1 1 d . . . . .
C19 C 0.24522(12) 0.80973(8) 0.68789(12) 0.0190(2) Uani 1 1 d . . . . .
H19 H 0.318437 0.820715 0.774383 0.023 Uiso 1 1 calc R U . . .
C20 C 0.16577(13) 0.88282(8) 0.61261(13) 0.0212(3) Uani 1 1 d . . . . .
C21 C 0.05552(13) 0.87133(8) 0.48840(13) 0.0215(3) Uani 1 1 d . . . . .
H21 H 0.002017 0.923024 0.438919 0.026 Uiso 1 1 calc R U . . .
C22 C 0.02546(12) 0.78165(8) 0.43825(12) 0.0189(2) Uani 1 1 d . . . . .
H22 H -0.051932 0.771794 0.353864 0.023 Uiso 1 1 calc R U . . .
C23 C 0.33810(14) 0.65265(9) 0.87256(12) 0.0239(3) Uani 1 1 d . . . . .
H23A H 0.376419 0.593908 0.919008 0.036 Uiso 1 1 calc R U . . .
H23B H 0.253470 0.669147 0.882807 0.036 Uiso 1 1 calc R U . . .
H23C H 0.408479 0.702026 0.910671 0.036 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
F24 C20 1.3551(14) . ?
O1 C12 1.2102(14) . ?
O2 C11 1.2080(15) . ?
N3 C5 1.4353(14) . ?
N3 C11 1.4091(14) . ?
N3 C12 1.3895(15) . ?
N4 C13 1.4610(14) . ?
N4 C17 1.2768(15) . ?
C5 C6 1.3900(16) . ?
C5 C10 1.3839(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3898(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3846(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.3916(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.3902(17) . ?
C10 H10 0.9500 . ?
C11 C14 1.4778(15) . ?
C12 C13 1.5270(14) . ?
C13 H13 1.0000 . ?
C13 C14 1.4951(15) . ?
C14 C15 1.3336(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.4584(16) . ?
C16 C18 1.4159(16) . ?
C16 C22 1.4022(16) . ?
C17 C18 1.5003(16) . ?
C17 C23 1.5094(16) . ?
C18 C19 1.3999(16) . ?
C19 H19 0.9500 . ?
C19 C20 1.3768(17) . ?
C20 C21 1.3763(18) . ?
C21 H21 0.9500 . ?
C21 C22 1.3845(17) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C11 N3 C5 123.99(10) . . ?
C12 N3 C5 122.61(9) . . ?
C12 N3 C11 113.39(9) . . ?
C17 N4 C13 118.53(10) . . ?
C6 C5 N3 118.76(10) . . ?
C10 C5 N3 119.86(10) . . ?
C10 C5 C6 121.37(11) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 C5 118.68(11) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.64(11) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.00(11) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.94(12) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 119.34(11) . . ?
C5 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O2 C11 N3 124.80(10) . . ?
O2 C11 C14 129.56(10) . . ?
N3 C11 C14 105.64(9) . . ?
O1 C12 N3 124.62(10) . . ?
O1 C12 C13 127.26(10) . . ?
N3 C12 C13 108.11(9) . . ?
N4 C13 C12 109.03(9) . . ?
N4 C13 H13 110.4 . . ?
N4 C13 C14 113.49(8) . . ?
C12 C13 H13 110.4 . . ?
C14 C13 C12 102.97(9) . . ?
C14 C13 H13 110.4 . . ?
C11 C14 C13 109.71(9) . . ?
C15 C14 C11 125.79(11) . . ?
C15 C14 C13 124.42(10) . . ?
C14 C15 H15 118.5 . . ?
C14 C15 C16 122.94(10) . . ?
C16 C15 H15 118.5 . . ?
C18 C16 C15 124.03(10) . . ?
C22 C16 C15 116.96(11) . . ?
C22 C16 C18 119.01(11) . . ?
N4 C17 C18 127.30(10) . . ?
N4 C17 C23 116.27(10) . . ?
C18 C17 C23 116.43(10) . . ?
C16 C18 C17 123.80(10) . . ?
C19 C18 C16 118.69(10) . . ?
C19 C18 C17 117.28(10) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.73(11) . . ?
C20 C19 H19 120.1 . . ?
F24 C20 C19 118.12(11) . . ?
F24 C20 C21 118.85(11) . . ?
C21 C20 C19 123.04(11) . . ?
C20 C21 H21 121.2 . . ?
C20 C21 C22 117.54(11) . . ?
C22 C21 H21 121.2 . . ?
C16 C22 H22 119.0 . . ?
C21 C22 C16 121.94(11) . . ?
C21 C22 H22 119.0 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
F24 C20 C21 C22 179.75(10) . . . . ?
O1 C12 C13 N4 -53.86(14) . . . . ?
O1 C12 C13 C14 -174.67(10) . . . . ?
O2 C11 C14 C13 -179.29(11) . . . . ?
O2 C11 C14 C15 -2.3(2) . . . . ?
N3 C5 C6 C7 177.13(10) . . . . ?
N3 C5 C10 C9 -177.65(11) . . . . ?
N3 C11 C14 C13 -0.06(12) . . . . ?
N3 C11 C14 C15 176.89(11) . . . . ?
N3 C12 C13 N4 124.74(9) . . . . ?
N3 C12 C13 C14 3.93(11) . . . . ?
N4 C13 C14 C11 -120.02(10) . . . . ?
N4 C13 C14 C15 62.98(14) . . . . ?
N4 C17 C18 C16 40.73(17) . . . . ?
N4 C17 C18 C19 -144.94(11) . . . . ?
C5 N3 C11 O2 2.09(17) . . . . ?
C5 N3 C11 C14 -177.19(10) . . . . ?
C5 N3 C12 O1 -5.73(17) . . . . ?
C5 N3 C12 C13 175.62(9) . . . . ?
C5 C6 C7 C8 0.87(18) . . . . ?
C6 C5 C10 C9 1.10(19) . . . . ?
C6 C7 C8 C9 0.41(19) . . . . ?
C7 C8 C9 C10 -0.96(19) . . . . ?
C8 C9 C10 C5 0.21(19) . . . . ?
C10 C5 C6 C7 -1.63(18) . . . . ?
C11 N3 C5 C6 109.80(12) . . . . ?
C11 N3 C5 C10 -71.41(15) . . . . ?
C11 N3 C12 O1 174.27(10) . . . . ?
C11 N3 C12 C13 -4.37(12) . . . . ?
C11 C14 C15 C16 -176.05(10) . . . . ?
C12 N3 C5 C6 -70.20(15) . . . . ?
C12 N3 C5 C10 108.59(13) . . . . ?
C12 N3 C11 O2 -177.91(11) . . . . ?
C12 N3 C11 C14 2.81(12) . . . . ?
C12 C13 C14 C11 -2.32(11) . . . . ?
C12 C13 C14 C15 -179.32(10) . . . . ?
C13 N4 C17 C18 1.46(16) . . . . ?
C13 N4 C17 C23 -178.28(9) . . . . ?
C13 C14 C15 C16 0.47(17) . . . . ?
C14 C15 C16 C18 -30.60(17) . . . . ?
C14 C15 C16 C22 149.21(11) . . . . ?
C15 C16 C18 C17 -6.85(16) . . . . ?
C15 C16 C18 C19 178.89(10) . . . . ?
C15 C16 C22 C21 -177.27(10) . . . . ?
C16 C18 C19 C20 -1.30(16) . . . . ?
C17 N4 C13 C12 -178.10(9) . . . . ?
C17 N4 C13 C14 -63.98(13) . . . . ?
C17 C18 C19 C20 -175.93(10) . . . . ?
C18 C16 C22 C21 2.56(16) . . . . ?
C18 C19 C20 F24 -178.16(10) . . . . ?
C18 C19 C20 C21 2.06(18) . . . . ?
C19 C20 C21 C22 -0.47(18) . . . . ?
C20 C21 C22 C16 -1.87(17) . . . . ?
C22 C16 C18 C17 173.35(10) . . . . ?
C22 C16 C18 C19 -0.91(15) . . . . ?
C23 C17 C18 C16 -139.53(11) . . . . ?
C23 C17 C18 C19 34.81(14) . . . . ?

_olex2_submission_original_sample_id KAI199
_olex2_submission_special_instructions 'No special instructions were received'
