# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ao_keb_dk_30e_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2155036'
loop_
_audit_author_name
_audit_author_address
'Andreas Orthaber'
;Uppsala University
Sweden
;
_audit_update_record             
;
2022-02-27 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-02-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H7 F N2 O'
_chemical_formula_sum            'C9 H7 F N2 O'
_chemical_formula_weight         178.17
_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                   5.2349(8)
_cell_length_b                   8.1302(13)
_cell_length_c                   18.418(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.160(3)
_cell_angle_gamma                90
_cell_volume                     783.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3582
_cell_measurement_temperature    180
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1558 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.9073.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13765
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.917
_diffrn_reflns_theta_min         2.212
_diffrn_ambient_temperature      180
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1564
_reflns_number_total             2051
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.066
_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)+(0.0626P)²+0.3863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1385
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C6(H6), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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 0.6520(2) 0.20615(14) 0.44877(6) 0.0438(3) Uani 1 1 d . . . . .
O1 O 0.2333(2) 0.40626(15) 0.44394(6) 0.0334(3) Uani 1 1 d . . . . .
N1 N 0.1712(2) 0.36459(16) 0.56462(6) 0.0258(3) Uani 1 1 d . . . . .
H1 H 0.035320 0.428212 0.561973 0.031 Uiso 1 1 calc R U . . .
N2 N 0.0197(3) 0.3078(2) 0.82099(8) 0.0350(4) Uani 1 1 d . . . . .
C9 C 0.2355(3) 0.29785(18) 0.63198(8) 0.0237(3) Uani 1 1 d . . . . .
C10 C 0.4513(3) 0.19454(18) 0.63754(8) 0.0253(3) Uani 1 1 d . . . . .
C8 C 0.0877(3) 0.33376(19) 0.69236(8) 0.0257(3) Uani 1 1 d . . . . .
H8 H -0.058375 0.402418 0.687262 0.031 Uiso 1 1 calc R U . . .
C7 C 0.1554(3) 0.26853(19) 0.76009(8) 0.0266(3) Uani 1 1 d . . . . .
C2 C 0.3016(3) 0.33940(19) 0.50238(8) 0.0270(3) Uani 1 1 d . . . . .
C6 C 0.3751(3) 0.1672(2) 0.76648(8) 0.0297(4) Uani 1 1 d . . . . .
H6 H 0.424241 0.123699 0.812553 0.036 Uiso 1 1 calc R U . . .
C5 C 0.5170(3) 0.1315(2) 0.70690(9) 0.0295(3) Uani 1 1 d . . . . .
H5 H 0.662885 0.062711 0.712314 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5198(3) 0.2320(2) 0.51023(9) 0.0301(4) Uani 1 1 d . . . . .
C4 C 0.5924(3) 0.16208(19) 0.57372(9) 0.0294(3) Uani 1 1 d . . . . .
H4 H 0.736927 0.091467 0.575913 0.035 Uiso 1 1 calc R U . . .
H2A H 0.056(4) 0.247(2) 0.8604(11) 0.035 Uiso 1 1 d . U . . .
H2B H -0.139(4) 0.350(3) 0.8130(12) 0.048(6) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0507(6) 0.0499(7) 0.0313(5) -0.0023(4) 0.0177(5) 0.0064(5)
O1 0.0429(7) 0.0392(7) 0.0181(5) 0.0005(4) 0.0007(4) 0.0017(5)
N1 0.0281(6) 0.0304(7) 0.0189(6) 0.0006(5) -0.0004(5) 0.0030(5)
N2 0.0387(8) 0.0470(9) 0.0192(6) 0.0052(6) 0.0031(5) 0.0014(7)
C9 0.0272(7) 0.0252(7) 0.0186(6) 0.0003(5) -0.0021(5) -0.0041(5)
C10 0.0266(7) 0.0243(7) 0.0251(7) 0.0001(6) -0.0002(6) -0.0026(6)
C8 0.0267(7) 0.0294(8) 0.0211(7) 0.0003(6) -0.0002(5) 0.0001(6)
C7 0.0278(7) 0.0295(8) 0.0223(7) 0.0009(6) -0.0008(5) -0.0063(6)
C2 0.0324(8) 0.0282(8) 0.0205(7) -0.0025(5) 0.0007(6) -0.0052(6)
C6 0.0332(8) 0.0313(8) 0.0245(7) 0.0075(6) -0.0037(6) -0.0037(6)
C5 0.0285(7) 0.0277(8) 0.0322(8) 0.0055(6) -0.0023(6) -0.0001(6)
C3 0.0326(8) 0.0320(8) 0.0261(7) -0.0046(6) 0.0074(6) -0.0031(6)
C4 0.0289(8) 0.0268(8) 0.0327(8) -0.0020(6) 0.0039(6) 0.0011(6)

_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 C3 1.3553(18) . ?
O1 C2 1.2515(19) . ?
N1 H1 0.8800 . ?
N1 C9 1.3892(18) . ?
N1 C2 1.3616(19) . ?
N2 C7 1.377(2) . ?
N2 H2A 0.90(2) . ?
N2 H2B 0.91(2) . ?
C9 C10 1.410(2) . ?
C9 C8 1.398(2) . ?
C10 C5 1.412(2) . ?
C10 C4 1.425(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.394(2) . ?
C7 C6 1.418(2) . ?
C2 C3 1.443(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.369(2) . ?
C5 H5 0.9500 . ?
C3 C4 1.348(2) . ?
C4 H4 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
C9 N1 H1 117.4 . . ?
C2 N1 H1 117.4 . . ?
C2 N1 C9 125.21(13) . . ?
C7 N2 H2A 115.3(13) . . ?
C7 N2 H2B 116.2(14) . . ?
H2A N2 H2B 121.2(19) . . ?
N1 C9 C10 118.48(13) . . ?
N1 C9 C8 120.05(14) . . ?
C8 C9 C10 121.47(13) . . ?
C9 C10 C5 117.51(14) . . ?
C9 C10 C4 118.57(14) . . ?
C5 C10 C4 123.91(14) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 C9 119.83(14) . . ?
C7 C8 H8 120.1 . . ?
N2 C7 C8 120.96(15) . . ?
N2 C7 C6 119.87(14) . . ?
C8 C7 C6 119.09(14) . . ?
O1 C2 N1 121.30(15) . . ?
O1 C2 C3 124.12(14) . . ?
N1 C2 C3 114.59(13) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.62(14) . . ?
C5 C6 H6 119.7 . . ?
C10 C5 H5 119.3 . . ?
C6 C5 C10 121.45(15) . . ?
C6 C5 H5 119.3 . . ?
F1 C3 C2 115.29(14) . . ?
C4 C3 F1 121.27(15) . . ?
C4 C3 C2 123.44(14) . . ?
C10 C4 H4 120.1 . . ?
C3 C4 C10 119.70(15) . . ?
C3 C4 H4 120.1 . . ?

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 C3 C4 C10 178.84(14) . . . . ?
O1 C2 C3 F1 0.0(2) . . . . ?
O1 C2 C3 C4 179.36(16) . . . . ?
N1 C9 C10 C5 178.42(13) . . . . ?
N1 C9 C10 C4 -0.5(2) . . . . ?
N1 C9 C8 C7 -179.01(13) . . . . ?
N1 C2 C3 F1 -179.80(13) . . . . ?
N1 C2 C3 C4 -0.4(2) . . . . ?
N2 C7 C6 C5 -177.80(15) . . . . ?
C9 N1 C2 O1 -178.87(14) . . . . ?
C9 N1 C2 C3 0.9(2) . . . . ?
C9 C10 C5 C6 0.8(2) . . . . ?
C9 C10 C4 C3 1.0(2) . . . . ?
C9 C8 C7 N2 177.10(14) . . . . ?
C9 C8 C7 C6 0.4(2) . . . . ?
C10 C9 C8 C7 0.9(2) . . . . ?
C8 C9 C10 C5 -1.5(2) . . . . ?
C8 C9 C10 C4 179.54(14) . . . . ?
C8 C7 C6 C5 -1.0(2) . . . . ?
C7 C6 C5 C10 0.4(2) . . . . ?
C2 N1 C9 C10 -0.4(2) . . . . ?
C2 N1 C9 C8 179.47(14) . . . . ?
C2 C3 C4 C10 -0.5(3) . . . . ?
C5 C10 C4 C3 -177.89(15) . . . . ?
C4 C10 C5 C6 179.73(15) . . . . ?

_shelx_res_file                  
;
TITL ao_keb_dk_30e_1_0m_a.res in P2(1)/c
    ao_keb_dk_30e_1_0m.res
    created by SHELXL-2018/3 at 15:36:57 on 22-Feb-2022
REM Old TITL AO_KEB_DK_30e_1_0m in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.141, Rweak 0.003, Alpha 0.014, Orientation as input
REM Formula found by SHELXT: C10 N O2
CELL 0.71073 5.2349 8.1302 18.4176 90 91.16 90
ZERR 4 0.0008 0.0013 0.0029 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N O
UNIT 36 28 4 8 4

L.S. 10
PLAN  5
SIZE 0.12 0.12 0.1
TEMP -93.15
CONF
BOND $H
list 4
fmap 2
MORE -1
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\AO_KEB_DK_30e_1_0m.hkl">
REM </olex2.extras>

WGHT    0.062600    0.386300
FVAR       0.65891
F1    3    0.652050    0.206153    0.448766    11.00000    0.05070    0.04995 =
         0.03130   -0.00235    0.01766    0.00645
O1    5    0.233286    0.406262    0.443938    11.00000    0.04289    0.03921 =
         0.01810    0.00048    0.00074    0.00165
N1    4    0.171180    0.364585    0.564623    11.00000    0.02806    0.03041 =
         0.01885    0.00061   -0.00041    0.00295
AFIX  43
H1    2    0.035320    0.428212    0.561973    11.00000   -1.20000
AFIX   0
N2    4    0.019711    0.307837    0.820987    11.00000    0.03874    0.04705 =
         0.01921    0.00515    0.00305    0.00145
C9    1    0.235505    0.297854    0.631984    11.00000    0.02724    0.02518 =
         0.01858    0.00029   -0.00215   -0.00414
C10   1    0.451332    0.194539    0.637541    11.00000    0.02659    0.02429 =
         0.02513    0.00010   -0.00016   -0.00261
C8    1    0.087730    0.333760    0.692365    11.00000    0.02666    0.02943 =
         0.02105    0.00033   -0.00018    0.00014
AFIX  43
H8    2   -0.058375    0.402418    0.687262    11.00000   -1.20000
AFIX   0
C7    1    0.155364    0.268530    0.760090    11.00000    0.02784    0.02955 =
         0.02225    0.00091   -0.00082   -0.00625
C2    1    0.301573    0.339396    0.502376    11.00000    0.03243    0.02819 =
         0.02045   -0.00245    0.00068   -0.00518
C6    1    0.375058    0.167204    0.766483    11.00000    0.03323    0.03131 =
         0.02449    0.00752   -0.00371   -0.00372
AFIX  43
H6    2    0.424241    0.123699    0.812553    11.00000   -1.20000
AFIX   0
C5    1    0.517000    0.131459    0.706899    11.00000    0.02848    0.02773 =
         0.03219    0.00549   -0.00234   -0.00013
AFIX  43
H5    2    0.662885    0.062711    0.712314    11.00000   -1.20000
AFIX   0
C3    1    0.519764    0.232030    0.510226    11.00000    0.03259    0.03202 =
         0.02609   -0.00463    0.00744   -0.00310
C4    1    0.592386    0.162079    0.573717    11.00000    0.02886    0.02676 =
         0.03272   -0.00197    0.00389    0.00114
AFIX  43
H4    2    0.736927    0.091467    0.575913    11.00000   -1.20000
AFIX   0
H2A   2    0.056279    0.246998    0.860448    11.00000   -1.20000
H2B   2   -0.139342    0.349828    0.812995    11.00000    0.04812
HKLF 4




REM  ao_keb_dk_30e_1_0m_a.res in P2(1)/c
REM wR2 = 0.138460, GooF = S = 1.06594, Restrained GooF = 1.06594 for all data
REM R1 = 0.044403 for 1564 Fo > 4sig(Fo) and 0.060625 for all 2051 data
REM 125 parameters refined using 0 restraints

END

WGHT      0.0626      0.3863

REM Highest difference peak  0.315,  deepest hole -0.211,  1-sigma level  0.049
Q1    1   0.5162  0.1827  0.6067  11.00000  0.05    0.32
Q2    1   0.4073  0.2892  0.5090  11.00000  0.05    0.31
Q3    1   0.2918  0.2367  0.7671  11.00000  0.05    0.31
Q4    1   0.3412  0.2412  0.6361  11.00000  0.05    0.30
Q5    1   0.1607  0.3130  0.6629  11.00000  0.05    0.29
;
_shelx_res_checksum              42477
_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_ao_keb_dk_31b_mecn_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2155038'
loop_
_audit_author_name
_audit_author_address
'Andreas Orthaber'
;Uppsala University
Sweden
;
_audit_update_record             
;
2022-02-27 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-02-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H7 F N2 O'
_chemical_formula_sum            'C9 H7 F N2 O'
_chemical_formula_weight         178.17
_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                   7.6379(14)
_cell_length_b                   6.7755(12)
_cell_length_c                   15.015(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.312(4)
_cell_angle_gamma                90
_cell_volume                     752.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2162
_cell_measurement_temperature    180
_cell_measurement_theta_max      25.491
_cell_measurement_theta_min      2.752
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1469 before and 0.0466 after correction.
The Ratio of minimum to maximum transmission is 0.9075.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10754
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.516
_diffrn_reflns_theta_min         2.752
_diffrn_ambient_temperature      180
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1277
_reflns_number_total             1798
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.067
_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)+(0.0795P)²+0.0755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1399
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C4(H4), C3(H3), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.53677(15) 0.18394(15) 0.39055(7) 0.0371(3) Uani 1 1 d . . . . .
O1 O 0.91156(17) 1.00546(18) 0.37924(8) 0.0327(4) Uani 1 1 d . . . . .
N1 N 0.86321(19) 0.7761(2) 0.48042(10) 0.0259(4) Uani 1 1 d . . . . .
H1 H 0.924568 0.850559 0.525449 0.031 Uiso 1 1 calc R U . . .
N2 N 0.8141(3) 0.2873(3) 0.70557(11) 0.0389(4) Uani 1 1 d . . . . .
C8 C 0.8375(2) 0.5365(2) 0.59483(11) 0.0260(4) Uani 1 1 d . . . . .
H8 H 0.905172 0.619400 0.641946 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7994(2) 0.5978(2) 0.50379(11) 0.0243(4) Uani 1 1 d . . . . .
C10 C 0.6951(2) 0.4809(2) 0.43154(12) 0.0251(4) Uani 1 1 d . . . . .
C2 C 0.8387(2) 0.8458(3) 0.39331(11) 0.0270(4) Uani 1 1 d . . . . .
C5 C 0.6377(2) 0.2987(3) 0.45833(12) 0.0289(4) Uani 1 1 d . . . . .
C4 C 0.6580(2) 0.5551(3) 0.34053(12) 0.0281(4) Uani 1 1 d . . . . .
H4 H 0.583191 0.480824 0.292139 0.034 Uiso 1 1 calc R U . . .
C3 C 0.7265(2) 0.7287(3) 0.32105(12) 0.0288(4) Uani 1 1 d . . . . .
H3 H 0.700598 0.774212 0.259334 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6751(2) 0.2321(3) 0.54589(12) 0.0297(4) Uani 1 1 d . . . . .
H6 H 0.634032 0.105885 0.559467 0.036 Uiso 1 1 calc R U . . .
C7 C 0.7765(2) 0.3535(3) 0.61717(12) 0.0282(4) Uani 1 1 d . . . . .
H2A H 0.853(3) 0.373(3) 0.7499(14) 0.034 Uiso 1 1 d . U . . .
H2B H 0.776(4) 0.160(4) 0.7197(19) 0.081(9) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0395(7) 0.0331(6) 0.0352(7) -0.0084(4) 0.0025(5) -0.0126(4)
O1 0.0433(8) 0.0248(7) 0.0264(7) 0.0021(5) 0.0020(6) -0.0042(5)
N1 0.0309(8) 0.0205(7) 0.0241(8) -0.0030(5) 0.0028(6) -0.0014(6)
N2 0.0551(11) 0.0340(9) 0.0291(9) -0.0003(7) 0.0133(8) -0.0083(8)
C8 0.0263(9) 0.0265(9) 0.0251(9) -0.0045(7) 0.0061(7) 0.0003(7)
C9 0.0220(8) 0.0237(8) 0.0272(9) -0.0036(7) 0.0062(7) 0.0035(6)
C10 0.0231(8) 0.0245(8) 0.0283(9) -0.0024(7) 0.0073(7) 0.0018(7)
C2 0.0285(9) 0.0255(9) 0.0251(9) -0.0016(7) 0.0028(7) 0.0048(7)
C5 0.0241(9) 0.0298(9) 0.0323(10) -0.0093(7) 0.0058(7) -0.0038(7)
C4 0.0248(9) 0.0317(9) 0.0260(9) -0.0075(7) 0.0030(7) 0.0007(7)
C3 0.0290(9) 0.0316(9) 0.0241(9) -0.0003(7) 0.0032(7) 0.0021(7)
C6 0.0313(9) 0.0232(9) 0.0375(11) 0.0003(7) 0.0140(8) -0.0046(7)
C7 0.0284(9) 0.0300(9) 0.0282(9) -0.0016(7) 0.0105(7) 0.0018(7)

_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 C5 1.3588(19) . ?
O1 C2 1.258(2) . ?
N1 H1 0.8800 . ?
N1 C9 1.380(2) . ?
N1 C2 1.359(2) . ?
N2 C7 1.363(2) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.95(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(2) . ?
C8 C7 1.395(2) . ?
C9 C10 1.418(2) . ?
C10 C5 1.402(2) . ?
C10 C4 1.417(2) . ?
C2 C3 1.443(2) . ?
C5 C6 1.352(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.348(3) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.418(2) . ?

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
C9 N1 H1 117.4 . . ?
C2 N1 H1 117.4 . . ?
C2 N1 C9 125.12(15) . . ?
C7 N2 H2A 118.3(14) . . ?
C7 N2 H2B 120.9(18) . . ?
H2A N2 H2B 120(2) . . ?
C9 C8 H8 120.0 . . ?
C9 C8 C7 120.10(16) . . ?
C7 C8 H8 120.0 . . ?
N1 C9 C8 120.71(15) . . ?
N1 C9 C10 117.47(15) . . ?
C8 C9 C10 121.82(16) . . ?
C5 C10 C9 115.38(16) . . ?
C5 C10 C4 125.94(16) . . ?
C4 C10 C9 118.68(15) . . ?
O1 C2 N1 119.92(15) . . ?
O1 C2 C3 123.49(16) . . ?
N1 C2 C3 116.59(16) . . ?
F1 C5 C10 116.65(16) . . ?
C6 C5 F1 118.81(16) . . ?
C6 C5 C10 124.54(16) . . ?
C10 C4 H4 119.2 . . ?
C3 C4 C10 121.52(16) . . ?
C3 C4 H4 119.2 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.45(16) . . ?
C4 C3 H3 119.8 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.01(16) . . ?
C7 C6 H6 120.5 . . ?
N2 C7 C8 121.62(16) . . ?
N2 C7 C6 119.26(17) . . ?
C8 C7 C6 119.12(16) . . ?

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 C5 C6 C7 -178.41(14) . . . . ?
O1 C2 C3 C4 177.51(16) . . . . ?
N1 C9 C10 C5 178.23(14) . . . . ?
N1 C9 C10 C4 -1.8(2) . . . . ?
N1 C2 C3 C4 -3.0(2) . . . . ?
C8 C9 C10 C5 -1.5(2) . . . . ?
C8 C9 C10 C4 178.51(15) . . . . ?
C9 N1 C2 O1 -175.94(15) . . . . ?
C9 N1 C2 C3 4.5(2) . . . . ?
C9 C8 C7 N2 178.85(16) . . . . ?
C9 C8 C7 C6 -0.2(2) . . . . ?
C9 C10 C5 F1 179.70(14) . . . . ?
C9 C10 C5 C6 0.1(3) . . . . ?
C9 C10 C4 C3 3.1(2) . . . . ?
C10 C5 C6 C7 1.2(3) . . . . ?
C10 C4 C3 C2 -0.7(3) . . . . ?
C2 N1 C9 C8 177.56(15) . . . . ?
C2 N1 C9 C10 -2.2(2) . . . . ?
C5 C10 C4 C3 -176.85(16) . . . . ?
C5 C6 C7 N2 179.81(16) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C4 C10 C5 F1 -0.3(3) . . . . ?
C4 C10 C5 C6 -179.88(17) . . . . ?
C7 C8 C9 N1 -178.16(15) . . . . ?
C7 C8 C9 C10 1.6(2) . . . . ?

_shelx_res_file                  
;
TITL ao_keb_dk_31b_mecn_2_0m_a.res in P2(1)/c
    ao_keb_dk_31b_mecn_2_0m.res
    created by SHELXL-2018/3 at 15:35:23 on 22-Feb-2022
REM Old TITL AO_KEB_DK_31B_MeCN_2_0m in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.134, Rweak 0.003, Alpha 0.024, Orientation as input
REM Formula found by SHELXT: C10 N O F
CELL 0.71073 7.6379 6.7755 15.0153 90 104.312 90
ZERR 4 0.0014 0.0012 0.0026 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N O
UNIT 36 28 4 8 4

L.S. 10
PLAN  5
SIZE 0.12 0.13 0.12
TEMP -93.15
CONF
BOND $H
list 4
fmap 2
acta
MORE -1
REM <olex2.extras>
REM <HklSrc "%.\\AO_KEB_DK_31B_MeCN_2_0m.hkl">
REM </olex2.extras>

WGHT    0.079500    0.075500
FVAR       0.89745
F1    3    0.536772    0.183944    0.390552    11.00000    0.03955    0.03305 =
         0.03522   -0.00837    0.00250   -0.01260
O1    5    0.911558    1.005455    0.379245    11.00000    0.04327    0.02485 =
         0.02641    0.00208    0.00203   -0.00416
N1    4    0.863214    0.776126    0.480422    11.00000    0.03092    0.02048 =
         0.02412   -0.00303    0.00276   -0.00140
AFIX  43
H1    2    0.924568    0.850559    0.525449    11.00000   -1.20000
AFIX   0
N2    4    0.814056    0.287323    0.705566    11.00000    0.05509    0.03398 =
         0.02914   -0.00026    0.01330   -0.00829
C8    1    0.837466    0.536514    0.594827    11.00000    0.02627    0.02654 =
         0.02508   -0.00452    0.00609    0.00027
AFIX  43
H8    2    0.905172    0.619400    0.641946    11.00000   -1.20000
AFIX   0
C9    1    0.799373    0.597797    0.503793    11.00000    0.02197    0.02372 =
         0.02717   -0.00364    0.00624    0.00354
C10   1    0.695067    0.480895    0.431542    11.00000    0.02307    0.02451 =
         0.02835   -0.00236    0.00728    0.00178
C2    1    0.838740    0.845763    0.393314    11.00000    0.02853    0.02548 =
         0.02511   -0.00164    0.00280    0.00479
C5    1    0.637695    0.298654    0.458334    11.00000    0.02410    0.02976 =
         0.03228   -0.00931    0.00578   -0.00378
C4    1    0.658001    0.555110    0.340529    11.00000    0.02483    0.03174 =
         0.02598   -0.00747    0.00299    0.00065
AFIX  43
H4    2    0.583191    0.480824    0.292139    11.00000   -1.20000
AFIX   0
C3    1    0.726459    0.728681    0.321052    11.00000    0.02904    0.03157 =
         0.02411   -0.00026    0.00322    0.00212
AFIX  43
H3    2    0.700598    0.774212    0.259334    11.00000   -1.20000
AFIX   0
C6    1    0.675070    0.232081    0.545888    11.00000    0.03134    0.02319 =
         0.03747    0.00031    0.01401   -0.00457
AFIX  43
H6    2    0.634032    0.105885    0.559467    11.00000   -1.20000
AFIX   0
C7    1    0.776462    0.353452    0.617169    11.00000    0.02840    0.02997 =
         0.02821   -0.00160    0.01052    0.00179
H2A   2    0.852885    0.372689    0.749934    11.00000   -1.20000
H2B   2    0.775907    0.159980    0.719691    11.00000    0.08133
HKLF 4




REM  ao_keb_dk_31b_mecn_2_0m_a.res in P2(1)/c
REM wR2 = 0.139871, GooF = S = 1.06675, Restrained GooF = 1.06675 for all data
REM R1 = 0.048422 for 1277 Fo > 4sig(Fo) and 0.071884 for all 1798 data
REM 125 parameters refined using 0 restraints

END

WGHT      0.0795      0.0716

REM Highest difference peak  0.468,  deepest hole -0.177,  1-sigma level  0.058
Q1    1   0.9431  0.8219  0.5978  11.00000  0.05    0.47
Q2    1   0.5979  0.0050  0.6220  11.00000  0.05    0.46
Q3    1   0.6576  0.1579  0.6036  11.00000  0.05    0.39
Q4    1   0.8355  0.4664  0.6576  11.00000  0.05    0.36
Q5    1   0.6857  0.3909  0.4788  11.00000  0.05    0.28
;
_shelx_res_checksum              1250
_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_ao_keb_dk_155_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2155037'
loop_
_audit_author_name
_audit_author_address
'Andreas Orthaber'
;Uppsala University
Sweden
;
_audit_update_record             
;
2022-02-27 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-02-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H7 F N2 O'
_chemical_formula_sum            'C9 H7 F N2 O'
_chemical_formula_weight         178.17
_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                   7.481(2)
_cell_length_b                   6.777(2)
_cell_length_c                   15.561(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.970(6)
_cell_angle_gamma                90
_cell_volume                     774.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2178
_cell_measurement_temperature    180
_cell_measurement_theta_max      26.628
_cell_measurement_theta_min      2.667
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1602 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.8288. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14239
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.936
_diffrn_reflns_theta_min         2.667
_diffrn_ambient_temperature      180
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1333
_reflns_number_total             2041
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.062
_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)+(0.0420P)²+0.4858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1304
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C8(H8), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.14546(18) 0.05803(18) 0.10341(8) 0.0443(4) Uani 1 1 d . . . . .
O1 O 0.4063(2) 0.9867(2) -0.11487(9) 0.0375(4) Uani 1 1 d . . . . .
N1 N 0.3632(2) 0.7700(2) -0.00982(10) 0.0278(4) Uani 1 1 d . . . . .
H1 H 0.422524 0.851009 0.029817 0.033 Uiso 1 1 calc R U . . .
C5 C 0.1521(3) 0.2793(3) -0.01334(13) 0.0322(5) Uani 1 1 d . . . . .
H5 H 0.086946 0.187114 -0.053516 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3410(3) 0.5467(3) 0.10859(12) 0.0272(4) Uani 1 1 d . . . . .
H8 H 0.402917 0.639252 0.149618 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3032(2) 0.5935(3) 0.01949(12) 0.0254(4) Uani 1 1 d . . . . .
C10 C 0.2055(2) 0.4628(3) -0.04308(12) 0.0277(4) Uani 1 1 d . . . . .
C4 C 0.1671(3) 0.5253(3) -0.13212(13) 0.0322(5) Uani 1 1 d . . . . .
H4 H 0.095932 0.442414 -0.174658 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2886(3) 0.3658(3) 0.13739(13) 0.0289(4) Uani 1 1 d . . . . .
C2 C 0.3377(3) 0.8285(3) -0.09519(12) 0.0301(4) Uani 1 1 d . . . . .
C6 C 0.1947(3) 0.2361(3) 0.07286(13) 0.0307(4) Uani 1 1 d . . . . .
N2 N 0.3255(3) 0.3080(3) 0.22290(13) 0.0421(5) Uani 1 1 d . . . . .
C3 C 0.2286(3) 0.6986(3) -0.15789(13) 0.0329(5) Uani 1 1 d . . . . .
H3 H 0.199861 0.735558 -0.217826 0.039 Uiso 1 1 calc R U . . .
H2A H 0.285(3) 0.201(4) 0.2357(14) 0.039 Uiso 1 1 d . U . . .
H2B H 0.360(3) 0.398(4) 0.2649(16) 0.050(7) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0529(8) 0.0301(7) 0.0515(8) -0.0036(6) 0.0140(6) -0.0149(6)
O1 0.0544(10) 0.0286(8) 0.0284(7) 0.0018(6) 0.0054(6) -0.0010(7)
N1 0.0340(9) 0.0219(8) 0.0270(8) -0.0057(6) 0.0042(7) 0.0002(7)
C5 0.0262(10) 0.0312(11) 0.0394(11) -0.0143(9) 0.0066(8) -0.0037(8)
C8 0.0299(10) 0.0238(9) 0.0279(10) -0.0070(7) 0.0055(8) -0.0005(8)
C9 0.0238(9) 0.0229(9) 0.0302(10) -0.0051(7) 0.0068(8) 0.0022(7)
C10 0.0226(9) 0.0293(10) 0.0315(10) -0.0093(8) 0.0055(8) 0.0014(7)
C4 0.0256(10) 0.0407(12) 0.0296(10) -0.0125(9) 0.0036(8) 0.0014(8)
C7 0.0286(10) 0.0271(10) 0.0322(10) -0.0042(8) 0.0091(8) 0.0005(8)
C2 0.0341(11) 0.0291(10) 0.0276(10) -0.0021(8) 0.0066(8) 0.0066(8)
C6 0.0295(10) 0.0231(9) 0.0415(12) -0.0039(8) 0.0118(9) -0.0042(8)
N2 0.0639(14) 0.0298(10) 0.0332(10) 0.0010(8) 0.0105(9) -0.0117(9)
C3 0.0344(11) 0.0390(11) 0.0244(10) -0.0028(8) 0.0035(8) 0.0054(9)

_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 C6 1.373(2) . ?
O1 C2 1.252(2) . ?
N1 H1 0.8800 . ?
N1 C9 1.385(2) . ?
N1 C2 1.364(2) . ?
C5 H5 0.9500 . ?
C5 C10 1.411(3) . ?
C5 C6 1.350(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.398(3) . ?
C8 C7 1.388(3) . ?
C9 C10 1.413(3) . ?
C10 C4 1.425(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.350(3) . ?
C7 C6 1.416(3) . ?
C7 N2 1.364(3) . ?
C2 C3 1.446(3) . ?
N2 H2A 0.83(2) . ?
N2 H2B 0.90(3) . ?
C3 H3 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
C9 N1 H1 117.4 . . ?
C2 N1 H1 117.4 . . ?
C2 N1 C9 125.26(16) . . ?
C10 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C6 C5 C10 119.26(17) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.29(17) . . ?
N1 C9 C8 120.35(17) . . ?
N1 C9 C10 118.17(17) . . ?
C8 C9 C10 121.47(18) . . ?
C5 C10 C9 117.92(18) . . ?
C5 C10 C4 124.29(18) . . ?
C9 C10 C4 117.78(18) . . ?
C10 C4 H4 119.0 . . ?
C3 C4 C10 122.02(18) . . ?
C3 C4 H4 119.0 . . ?
C8 C7 C6 116.87(18) . . ?
N2 C7 C8 123.46(18) . . ?
N2 C7 C6 119.66(18) . . ?
O1 C2 N1 119.94(18) . . ?
O1 C2 C3 124.17(18) . . ?
N1 C2 C3 115.89(18) . . ?
F1 C6 C7 115.43(18) . . ?
C5 C6 F1 120.43(17) . . ?
C5 C6 C7 124.14(18) . . ?
C7 N2 H2A 118.2(16) . . ?
C7 N2 H2B 119.4(16) . . ?
H2A N2 H2B 120(2) . . ?
C4 C3 C2 120.66(18) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.88 1.99 2.861(2) 170.5 3_675 yes
N1 H1 N1 0.88 3.07 3.710(3) 130.8 3_675 yes
N1 H1 C2 0.88 2.88 3.700(3) 156.4 3_675 yes
C5 H5 F1 0.95 2.42 3.310(2) 155.3 3 yes
C5 H5 C6 0.95 3.54 4.344(3) 144.3 3 yes
C8 H8 O1 0.95 3.01 3.675(3) 128.5 3_675 yes
C8 H8 N2 0.95 2.80 3.707(3) 160.2 2_655 yes
C4 H4 F1 0.95 3.54 4.126(3) 122.1 4_565 yes
C3 H3 F1 0.95 3.38 4.041(3) 128.4 4_565 yes
C3 H3 C8 0.95 3.42 4.249(3) 147.6 4_575 yes
N2 H2A C4 0.83(2) 2.84(2) 3.551(3) 145.9(19) 4_566 yes
N2 H2A C3 0.83(2) 3.24(2) 4.033(3) 161(2) 4_566 yes
N2 H2B O1 0.90(3) 1.99(3) 2.845(3) 157(2) 4_576 yes
N2 H2B C2 0.90(3) 2.89(3) 3.740(3) 159(2) 4_576 yes
N2 H2B C3 0.90(3) 3.21(3) 3.957(3) 142(2) 4_576 yes

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 C2 C3 C4 176.56(19) . . . . ?
N1 C9 C10 C5 177.11(16) . . . . ?
N1 C9 C10 C4 -3.1(3) . . . . ?
N1 C2 C3 C4 -3.9(3) . . . . ?
C5 C10 C4 C3 -176.82(19) . . . . ?
C8 C9 C10 C5 -2.1(3) . . . . ?
C8 C9 C10 C4 177.71(17) . . . . ?
C8 C7 C6 F1 179.72(16) . . . . ?
C8 C7 C6 C5 -0.9(3) . . . . ?
C9 N1 C2 O1 -176.15(18) . . . . ?
C9 N1 C2 C3 4.3(3) . . . . ?
C9 C8 C7 C6 -0.8(3) . . . . ?
C9 C8 C7 N2 178.05(19) . . . . ?
C9 C10 C4 C3 3.4(3) . . . . ?
C10 C5 C6 F1 -179.54(17) . . . . ?
C10 C5 C6 C7 1.1(3) . . . . ?
C10 C4 C3 C2 0.2(3) . . . . ?
C7 C8 C9 N1 -176.85(17) . . . . ?
C7 C8 C9 C10 2.4(3) . . . . ?
C2 N1 C9 C8 178.42(18) . . . . ?
C2 N1 C9 C10 -0.8(3) . . . . ?
C6 C5 C10 C9 0.4(3) . . . . ?
C6 C5 C10 C4 -179.43(19) . . . . ?
N2 C7 C6 F1 0.8(3) . . . . ?
N2 C7 C6 C5 -179.9(2) . . . . ?

_shelx_res_file                  
;
TITL AO_KEB_DK_155_1_0m in P21/c #14
    ao_keb_dk_155_1_0m.res
    created by SHELXL-2018/3 at 16:10:27 on 22-Feb-2022
REM reset to P21/c #14
CELL 0.71073 7.4814 6.7767 15.5606 90 100.9703 90
ZERR 4 0.0024 0.0022 0.0051 0 0.006 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N O
UNIT 36 28 4 8 4
EQIV $1 1-X,2-Y,-Z
EQIV $2 +X,1.5-Y,0.5+Z
EQIV $3 -X,-Y,-Z
EQIV $4 1-X,0.5+Y,0.5-Z
EQIV $5 +X,0.5-Y,-0.5+Z
EQIV $6 +X,0.5-Y,0.5+Z
EQIV $7 +X,1.5-Y,-0.5+Z

L.S. 12
PLAN  5
SIZE 0.16 0.15 0.09
TEMP -93.15
CONF
HTAB N1 O1_$1
HTAB N2 O1_$2
HTAB N1 N1_$1
HTAB N1 C2_$1
HTAB C5 F1_$3
HTAB C5 C6_$3
HTAB C8 O1_$1
HTAB C8 N2_$4
HTAB C8 C3_$2
HTAB C4 F1_$5
HTAB N2 C10_$6
HTAB N2 C4_$6
HTAB N2 C2_$2
HTAB N2 N2_$4
HTAB N2 C3_$6
HTAB N2 C3_$2
HTAB C3 F1_$5
HTAB C3 C8_$7
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\AO_KEB_DK_155_1_0m.hkl">
REM </olex2.extras>

WGHT    0.042000    0.485800
FVAR       0.25957
F1    3    0.145461    0.058026    0.103415    11.00000    0.05295    0.03011 =
         0.05149   -0.00361    0.01397   -0.01494
O1    5    0.406287    0.986715   -0.114866    11.00000    0.05443    0.02862 =
         0.02839    0.00180    0.00542   -0.00103
N1    4    0.363182    0.770031   -0.009818    11.00000    0.03402    0.02190 =
         0.02700   -0.00572    0.00423    0.00017
AFIX  43
H1    2    0.422524    0.851009    0.029817    11.00000   -1.20000
AFIX   0
C5    1    0.152131    0.279263   -0.013344    11.00000    0.02619    0.03118 =
         0.03939   -0.01433    0.00662   -0.00372
AFIX  43
H5    2    0.086946    0.187114   -0.053516    11.00000   -1.20000
AFIX   0
C8    1    0.341020    0.546742    0.108591    11.00000    0.02992    0.02376 =
         0.02790   -0.00697    0.00550   -0.00052
AFIX  43
H8    2    0.402917    0.639252    0.149618    11.00000   -1.20000
AFIX   0
C9    1    0.303183    0.593505    0.019490    11.00000    0.02380    0.02293 =
         0.03018   -0.00509    0.00679    0.00216
C10   1    0.205548    0.462779   -0.043078    11.00000    0.02257    0.02927 =
         0.03146   -0.00927    0.00548    0.00141
C4    1    0.167062    0.525266   -0.132120    11.00000    0.02558    0.04070 =
         0.02962   -0.01249    0.00364    0.00140
AFIX  43
H4    2    0.095932    0.442414   -0.174658    11.00000   -1.20000
AFIX   0
C7    1    0.288563    0.365753    0.137393    11.00000    0.02862    0.02715 =
         0.03220   -0.00424    0.00911    0.00053
C2    1    0.337695    0.828486   -0.095188    11.00000    0.03405    0.02906 =
         0.02757   -0.00211    0.00661    0.00663
C6    1    0.194697    0.236066    0.072856    11.00000    0.02954    0.02312 =
         0.04146   -0.00385    0.01176   -0.00421
N2    4    0.325516    0.308000    0.222904    11.00000    0.06386    0.02976 =
         0.03319    0.00098    0.01053   -0.01168
C3    1    0.228567    0.698578   -0.157891    11.00000    0.03442    0.03902 =
         0.02443   -0.00275    0.00350    0.00539
AFIX  43
H3    2    0.199861    0.735558   -0.217826    11.00000   -1.20000
AFIX   0
H2A   2    0.285134    0.200514    0.235734    11.00000   -1.20000
H2B   2    0.360456    0.398413    0.264925    11.00000    0.05003
HKLF 4




REM  AO_KEB_DK_155_1_0m in P21/c #14
REM wR2 = 0.130406, GooF = S = 1.06214, Restrained GooF = 1.06214 for all data
REM R1 = 0.051587 for 1333 Fo > 4sig(Fo) and 0.093564 for all 2041 data
REM 125 parameters refined using 0 restraints

END

WGHT      0.0420      0.4858

REM Highest difference peak  0.237,  deepest hole -0.253,  1-sigma level  0.049
Q1    1   0.3383  0.5527  0.0585  11.00000  0.05    0.24
Q2    1   0.2347  0.4676 -0.0819  11.00000  0.05    0.23
Q3    1   0.1843  0.3841 -0.0182  11.00000  0.05    0.22
Q4    1   0.1532  0.4855 -0.0813  11.00000  0.05    0.21
Q5    1   0.2968  0.7440 -0.1993  11.00000  0.05    0.21
;
_shelx_res_checksum              13515
_olex2_submission_special_instructions 'No special instructions were received'
