# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
# 
#######################################################################

data_rkn_922
_database_code_depnum_ccdc_archive 'CCDC 2277847'
loop_
_audit_author_name
_audit_author_address
'Anatoly Mishnev'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 F O S'
_chemical_formula_sum            'C11 H9 F O S'
_chemical_formula_weight         208.24

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3460(3)
_cell_length_b                   13.5411(6)
_cell_length_c                   9.8815(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.134(5)
_cell_angle_gamma                90
_cell_volume                     928.64(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5358
_cell_measurement_theta_min      5.7060
_cell_measurement_theta_max      74.9720

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.915
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.33894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7838
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.757
_diffrn_reflns_theta_max         75.772
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1779
_reflns_number_gt                1631
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1027P)²+0.2309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1779
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1451
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.44151(19) 0.40777(10) 0.13048(13) 0.0458(4) Uani 1 1 d . . . . .
S9 S 0.66690(6) 0.36815(3) 0.41248(5) 0.0285(2) Uani 1 1 d . . . . .
O11 O 0.5511(2) 0.68543(12) 0.29084(16) 0.0411(4) Uani 1 1 d . . . . .
C8 C 0.8134(3) 0.41160(15) 0.5783(2) 0.0268(4) Uani 1 1 d . . . . .
C3 C 0.8222(2) 0.51553(16) 0.58172(19) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.7049(3) 0.55811(15) 0.4453(2) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.9116(3) 0.35258(16) 0.6953(2) 0.0302(5) Uani 1 1 d . . . . .
H7 H 0.901994 0.282635 0.689604 0.036 Uiso 1 1 calc R U . . .
C5 C 1.0346(3) 0.50147(16) 0.8260(2) 0.0302(4) Uani 1 1 d . . . . .
H5 H 1.112295 0.531822 0.912267 0.036 Uiso 1 1 calc R U . . .
C10 C 0.6746(2) 0.66391(17) 0.4046(2) 0.0280(5) Uani 1 1 d . . . . .
C1 C 0.6149(3) 0.48662(14) 0.3478(2) 0.0263(4) Uani 1 1 d . . . . .
C13 C 0.4836(3) 0.50036(15) 0.1965(2) 0.0304(5) Uani 1 1 d . . . . .
H13A H 0.363090 0.533205 0.196232 0.037 Uiso 1 1 calc R U . . .
H13B H 0.546863 0.542606 0.143265 0.037 Uiso 1 1 calc R U . . .
C4 C 0.9365(3) 0.56043(15) 0.7111(2) 0.0280(4) Uani 1 1 d . . . . .
H4 H 0.945589 0.630320 0.718820 0.034 Uiso 1 1 calc R U . . .
C6 C 1.0229(3) 0.39845(16) 0.8189(2) 0.0316(5) Uani 1 1 d . . . . .
H6 H 1.091978 0.359972 0.899849 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7923(3) 0.74309(15) 0.4979(2) 0.0343(5) Uani 1 1 d . . . . .
H12A H 0.771708 0.805563 0.444996 0.052 Uiso 1 1 calc R U . . .
H12B H 0.929006 0.725193 0.526843 0.052 Uiso 1 1 calc R U . . .
H12C H 0.753599 0.750521 0.583333 0.052 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
F1 C13 1.400(2) . ?
S9 C1 1.723(2) . ?
S9 C8 1.742(2) . ?
O11 C10 1.226(2) . ?
C8 C7 1.396(3) . ?
C8 C3 1.409(3) . ?
C3 C4 1.416(3) . ?
C3 C2 1.459(3) . ?
C2 C1 1.373(3) . ?
C2 C10 1.485(3) . ?
C7 C6 1.375(3) . ?
C7 H7 0.9500 . ?
C5 C4 1.382(3) . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C10 C12 1.492(3) . ?
C1 C13 1.502(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C1 S9 C8 91.60(9) . . ?
C7 C8 C3 123.03(18) . . ?
C7 C8 S9 125.30(16) . . ?
C3 C8 S9 111.67(14) . . ?
C8 C3 C4 117.36(18) . . ?
C8 C3 C2 111.35(16) . . ?
C4 C3 C2 131.29(19) . . ?
C1 C2 C3 111.86(18) . . ?
C1 C2 C10 119.65(18) . . ?
C3 C2 C10 128.49(17) . . ?
C6 C7 C8 118.18(19) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C4 C5 C6 121.91(18) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
O11 C10 C2 118.57(19) . . ?
O11 C10 C12 120.1(2) . . ?
C2 C10 C12 121.36(17) . . ?
C2 C1 C13 128.02(19) . . ?
C2 C1 S9 113.50(15) . . ?
C13 C1 S9 118.47(14) . . ?
F1 C13 C1 108.94(16) . . ?
F1 C13 H13A 109.9 . . ?
C1 C13 H13A 109.9 . . ?
F1 C13 H13B 109.9 . . ?
C1 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C5 C4 C3 119.26(19) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C7 C6 C5 120.26(18) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_rkn_673
_database_code_depnum_ccdc_archive 'CCDC 2277848'
loop_
_audit_author_name
_audit_author_address
'Anatoly Mishnev'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H7 F N2 O'
_chemical_formula_weight         178.17

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.25810(10)
_cell_length_b                   8.4237(2)
_cell_length_c                   10.9697(3)
_cell_angle_alpha                94.118(2)
_cell_angle_beta                 98.142(2)
_cell_angle_gamma                94.746(2)
_cell_volume                     386.776(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4337
_cell_measurement_theta_min      4.0580
_cell_measurement_theta_max      75.9420

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.014
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7180
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.086
_diffrn_reflns_theta_max         76.152
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1532
_reflns_number_gt                1366
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²+0.0531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1532
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F12 F 0.61360(19) 0.84862(9) 0.44088(7) 0.0452(3) Uani 1 1 d . . . . .
O13 O 0.04212(19) 0.66411(10) 0.11637(7) 0.0325(3) Uani 1 1 d . . . . .
N2 N 0.6423(2) 0.55285(11) 0.34658(9) 0.0255(3) Uani 1 1 d . . . . .
N9 N 0.3116(2) 0.44100(11) 0.11571(8) 0.0279(3) Uani 1 1 d . . . . .
H9 H 0.211071 0.406428 0.041688 0.033 Uiso 1 1 calc R U . . .
C1 C 0.4370(3) 0.63537(14) 0.28815(10) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.6899(3) 0.40456(13) 0.29184(10) 0.0253(3) Uani 1 1 d . . . . .
C10 C 0.2462(3) 0.58235(14) 0.16685(10) 0.0266(3) Uani 1 1 d . . . . .
C8 C 0.5297(3) 0.34744(14) 0.17411(11) 0.0263(3) Uani 1 1 d . . . . .
C4 C 0.9060(3) 0.31070(14) 0.35526(10) 0.0276(3) Uani 1 1 d . . . . .
H4 H 1.015096 0.348091 0.435060 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3799(3) 0.79734(14) 0.34181(11) 0.0305(3) Uani 1 1 d . . . . .
H11A H 0.381727 0.874350 0.277795 0.037 Uiso 1 1 calc R U . . .
H11B H 0.168162 0.792307 0.369471 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9592(3) 0.16484(15) 0.30173(11) 0.0317(3) Uani 1 1 d . . . . .
H5 H 1.102783 0.100638 0.345177 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5895(3) 0.20035(15) 0.11897(11) 0.0309(3) Uani 1 1 d . . . . .
H7 H 0.484931 0.163017 0.038473 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8020(3) 0.11027(15) 0.18291(12) 0.0324(3) Uani 1 1 d . . . . .
H6 H 0.842842 0.009909 0.146191 0.039 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
F12 C11 1.3830(14) . ?
O13 C10 1.2465(14) . ?
N2 C1 1.2897(15) . ?
N2 C3 1.3895(15) . ?
N9 C10 1.3465(15) . ?
N9 C8 1.3853(15) . ?
N9 H9 0.8800 . ?
C1 C10 1.4760(16) . ?
C1 C11 1.4991(16) . ?
C3 C8 1.4041(17) . ?
C3 C4 1.4048(16) . ?
C8 C7 1.3979(17) . ?
C4 C5 1.3734(17) . ?
C4 H4 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C5 C6 1.4050(17) . ?
C5 H5 0.9500 . ?
C7 C6 1.3773(17) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C3 118.17(10) . . ?
C10 N9 C8 123.10(10) . . ?
C10 N9 H9 118.4 . . ?
C8 N9 H9 118.4 . . ?
N2 C1 C10 124.36(11) . . ?
N2 C1 C11 120.47(10) . . ?
C10 C1 C11 115.17(10) . . ?
N2 C3 C8 121.46(11) . . ?
N2 C3 C4 119.17(10) . . ?
C8 C3 C4 119.36(11) . . ?
O13 C10 N9 123.22(10) . . ?
O13 C10 C1 121.82(11) . . ?
N9 C10 C1 114.95(10) . . ?
N9 C8 C7 121.66(10) . . ?
N9 C8 C3 117.83(11) . . ?
C7 C8 C3 120.50(11) . . ?
C5 C4 C3 119.92(11) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
F12 C11 C1 110.12(9) . . ?
F12 C11 H11A 109.6 . . ?
C1 C11 H11A 109.6 . . ?
F12 C11 H11B 109.6 . . ?
C1 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
C4 C5 C6 120.20(11) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C6 C7 C8 119.11(11) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C6 C5 120.88(11) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_rkn_689
_database_code_depnum_ccdc_archive 'CCDC 2277855'
loop_
_audit_author_name
_audit_author_address
'Anatoly Mishnev'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 F2 N3 O2'
_chemical_formula_weight         329.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   16.6303(5)
_cell_length_b                   4.6620(2)
_cell_length_c                   18.9217(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.227(3)
_cell_angle_gamma                90
_cell_volume                     1433.73(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7760
_cell_measurement_theta_min      2.7160
_cell_measurement_theta_max      75.8780

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.021
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13626
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.719
_diffrn_reflns_theta_max         76.532
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2827
_reflns_number_gt                2260
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+1.2833P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2827
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F16 F 0.04834(9) 0.8768(4) 0.32519(8) 0.0610(5) Uani 1 1 d . . . . .
F24 F 0.72218(9) 0.3273(5) 0.73542(11) 0.0907(7) Uani 1 1 d . . . . .
O17 O 0.21888(11) 0.2286(4) 0.38102(13) 0.0676(6) Uani 1 1 d . . . . .
N14 N 0.41511(11) 0.0033(4) 0.58325(13) 0.0531(6) Uani 1 1 d . . . . .
H14 H 0.404072 -0.181270 0.579147 0.064 Uiso 1 1 calc R U . . .
N1 N 0.20862(12) 0.2525(4) 0.49947(14) 0.0547(6) Uani 1 1 d . . . . .
N2 N 0.09036(11) 0.6837(4) 0.45999(11) 0.0429(5) Uani 1 1 d . . . . .
O13 O 0.36293(12) 0.4461(4) 0.55438(19) 0.1028(11) Uani 1 1 d . . . . .
C3 C 0.12458(13) 0.5623(5) 0.41241(14) 0.0461(6) Uani 1 1 d . . . . .
C5 C 0.11206(13) 0.5893(5) 0.53090(14) 0.0450(6) Uani 1 1 d . . . . .
C6 C 0.07319(15) 0.7136(6) 0.58172(14) 0.0505(6) Uani 1 1 d . . . . .
H6 H 0.032943 0.858561 0.567152 0.061 Uiso 1 1 calc R U . . .
C2 C 0.18719(14) 0.3339(5) 0.42815(17) 0.0530(7) Uani 1 1 d . . . . .
C10 C 0.17188(14) 0.3744(5) 0.55222(16) 0.0526(7) Uani 1 1 d . . . . .
C18 C 0.49589(13) 0.0861(6) 0.62069(15) 0.0518(7) Uani 1 1 d . . . . .
C15 C 0.10378(15) 0.6514(6) 0.33560(15) 0.0536(6) Uani 1 1 d . . . . .
H15A H 0.154585 0.710290 0.320109 0.064 Uiso 1 1 calc R U . . .
H15B H 0.079776 0.486617 0.305351 0.064 Uiso 1 1 calc R U . . .
C7 C 0.09275(17) 0.6276(7) 0.65290(16) 0.0616(8) Uani 1 1 d . . . . .
H7 H 0.066019 0.711532 0.687497 0.074 Uiso 1 1 calc R U . . .
C9 C 0.19207(17) 0.2925(7) 0.62463(18) 0.0654(9) Uani 1 1 d . . . . .
H9 H 0.233300 0.151583 0.640061 0.079 Uiso 1 1 calc R U . . .
C21 C 0.64809(15) 0.2413(8) 0.69632(17) 0.0674(9) Uani 1 1 d . . . . .
C12 C 0.35556(15) 0.1851(5) 0.5542(2) 0.0648(9) Uani 1 1 d . . . . .
C11 C 0.27444(14) 0.0411(6) 0.5183(2) 0.0670(9) Uani 1 1 d . . . . .
H11A H 0.281550 -0.059964 0.473970 0.080 Uiso 1 1 calc R U . . .
H11B H 0.259247 -0.102741 0.551628 0.080 Uiso 1 1 calc R U . . .
C8 C 0.15247(19) 0.4153(7) 0.67363(18) 0.0709(9) Uani 1 1 d . . . . .
H8 H 0.165874 0.354792 0.722668 0.085 Uiso 1 1 calc R U . . .
C23 C 0.54127(18) 0.2822(10) 0.5929(2) 0.0839(11) Uani 1 1 d . . . . .
H23 H 0.520076 0.363351 0.546681 0.101 Uiso 1 1 calc R U . . .
C22 C 0.61830(18) 0.3650(10) 0.6316(2) 0.0916(12) Uani 1 1 d . . . . .
H22 H 0.649406 0.505925 0.612832 0.110 Uiso 1 1 calc R U . . .
C19 C 0.5277(2) -0.0349(10) 0.6865(2) 0.0974(13) Uani 1 1 d . . . . .
H19 H 0.496555 -0.172955 0.706171 0.117 Uiso 1 1 calc R U . . .
C20 C 0.6060(2) 0.0438(11) 0.7251(2) 0.1051(15) Uani 1 1 d . . . . .
H20 H 0.628817 -0.040825 0.770617 0.126 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
F16 C15 1.384(3) . ?
F24 C21 1.357(3) . ?
O17 C2 1.230(3) . ?
N14 C12 1.330(3) . ?
N14 C18 1.433(3) . ?
N14 H14 0.8800 . ?
N1 C2 1.374(4) . ?
N1 C10 1.397(4) . ?
N1 C11 1.460(3) . ?
N2 C3 1.293(3) . ?
N2 C5 1.385(3) . ?
O13 C12 1.223(3) . ?
C3 C2 1.475(3) . ?
C3 C15 1.480(4) . ?
C5 C6 1.393(4) . ?
C5 C10 1.409(3) . ?
C6 C7 1.376(4) . ?
C6 H6 0.9500 . ?
C10 C9 1.393(4) . ?
C18 C23 1.360(5) . ?
C18 C19 1.368(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C7 C8 1.398(5) . ?
C7 H7 0.9500 . ?
C9 C8 1.371(5) . ?
C9 H9 0.9500 . ?
C21 C20 1.340(6) . ?
C21 C22 1.350(5) . ?
C12 C11 1.531(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 H8 0.9500 . ?
C23 C22 1.388(4) . ?
C23 H23 0.9500 . ?
C22 H22 0.9500 . ?
C19 C20 1.401(4) . ?
C19 H19 0.9500 . ?
C20 H20 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
C12 N14 C18 124.8(2) . . ?
C12 N14 H14 117.6 . . ?
C18 N14 H14 117.6 . . ?
C2 N1 C10 121.8(2) . . ?
C2 N1 C11 116.8(3) . . ?
C10 N1 C11 121.3(3) . . ?
C3 N2 C5 118.2(2) . . ?
N2 C3 C2 124.8(2) . . ?
N2 C3 C15 121.0(2) . . ?
C2 C3 C15 114.1(2) . . ?
N2 C5 C6 118.2(2) . . ?
N2 C5 C10 121.8(2) . . ?
C6 C5 C10 120.0(2) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O17 C2 N1 122.7(2) . . ?
O17 C2 C3 122.3(3) . . ?
N1 C2 C3 115.0(2) . . ?
C9 C10 N1 122.7(3) . . ?
C9 C10 C5 119.0(3) . . ?
N1 C10 C5 118.3(2) . . ?
C23 C18 C19 119.3(3) . . ?
C23 C18 N14 121.9(3) . . ?
C19 C18 N14 118.7(3) . . ?
F16 C15 C3 111.3(2) . . ?
F16 C15 H15A 109.4 . . ?
C3 C15 H15A 109.4 . . ?
F16 C15 H15B 109.4 . . ?
C3 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C20 C21 C22 122.7(3) . . ?
C20 C21 F24 118.2(3) . . ?
C22 C21 F24 119.0(3) . . ?
O13 C12 N14 124.6(2) . . ?
O13 C12 C11 121.0(2) . . ?
N14 C12 C11 114.4(2) . . ?
N1 C11 C12 110.9(2) . . ?
N1 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C18 C23 C22 120.6(4) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C21 C22 C23 118.6(4) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C18 C19 C20 120.3(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 118.4(4) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_rkn_705
_database_code_depnum_ccdc_archive 'CCDC 2277849'
loop_
_audit_author_name
_audit_author_address
'Anatoly Mishnev'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 Cl F N2'
_chemical_formula_weight         196.61

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7276(4)
_cell_length_b                   7.3697(4)
_cell_length_c                   9.4118(5)
_cell_angle_alpha                72.213(5)
_cell_angle_beta                 73.348(5)
_cell_angle_gamma                69.557(5)
_cell_volume                     407.80(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4468
_cell_measurement_theta_min      4.9900
_cell_measurement_theta_max      75.1350

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    3.873
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7362
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.038
_diffrn_reflns_theta_max         75.589
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1599
_reflns_number_gt                1454
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1287P)²+0.0058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1599
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1624
_refine_ls_wR_factor_gt          0.1572
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl11 Cl 0.35487(8) 0.14683(7) 0.12858(5) 0.0347(3) Uani 1 1 d . . . . .
F13 F 0.6783(2) 0.39425(18) 0.11442(14) 0.0366(4) Uani 1 1 d . . . . .
N2 N 0.1334(3) 0.2013(2) 0.3951(2) 0.0274(4) Uani 1 1 d . . . . .
N9 N 0.4763(3) 0.2614(2) 0.4739(2) 0.0271(4) Uani 1 1 d . . . . .
C8 C 0.2797(3) 0.2722(3) 0.5725(2) 0.0261(5) Uani 1 1 d . . . . .
C3 C 0.1068(3) 0.2421(3) 0.5328(2) 0.0259(5) Uani 1 1 d . . . . .
C10 C 0.4977(3) 0.2251(3) 0.3419(3) 0.0269(5) Uani 1 1 d . . . . .
C7 C 0.2477(3) 0.3163(3) 0.7146(3) 0.0298(5) Uani 1 1 d . . . . .
H7 H 0.362094 0.336755 0.742287 0.036 Uiso 1 1 calc R U . . .
C1 C 0.3211(3) 0.1951(3) 0.3050(2) 0.0267(5) Uani 1 1 d . . . . .
C12 C 0.7105(3) 0.2224(3) 0.2314(2) 0.0296(5) Uani 1 1 d . . . . .
H12A H 0.820147 0.218848 0.284180 0.036 Uiso 1 1 calc R U . . .
H12B H 0.763277 0.102761 0.188812 0.036 Uiso 1 1 calc R U . . .
C4 C -0.0946(3) 0.2564(3) 0.6357(3) 0.0296(5) Uani 1 1 d . . . . .
H4 H -0.210840 0.236512 0.609866 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0512(4) 0.3295(3) 0.8122(3) 0.0313(5) Uani 1 1 d . . . . .
H6 H 0.029745 0.359464 0.907745 0.038 Uiso 1 1 calc R U . . .
C5 C -0.1209(3) 0.2990(3) 0.7729(3) 0.0315(5) Uani 1 1 d . . . . .
H5 H -0.256011 0.308177 0.842405 0.038 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
Cl11 C1 1.739(2) . ?
F13 C12 1.398(2) . ?
N2 C1 1.298(3) . ?
N2 C3 1.368(3) . ?
N9 C10 1.308(3) . ?
N9 C8 1.373(3) . ?
C8 C7 1.412(3) . ?
C8 C3 1.421(3) . ?
C3 C4 1.412(3) . ?
C10 C1 1.431(3) . ?
C10 C12 1.507(3) . ?
C7 C6 1.368(3) . ?
C7 H7 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C4 C5 1.370(3) . ?
C4 H4 0.9500 . ?
C6 C5 1.416(3) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C3 116.27(18) . . ?
C10 N9 C8 117.62(18) . . ?
N9 C8 C7 119.50(19) . . ?
N9 C8 C3 121.0(2) . . ?
C7 C8 C3 119.47(19) . . ?
N2 C3 C4 119.69(19) . . ?
N2 C3 C8 120.48(19) . . ?
C4 C3 C8 119.8(2) . . ?
N9 C10 C1 120.18(19) . . ?
N9 C10 C12 117.43(18) . . ?
C1 C10 C12 122.37(19) . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N2 C1 C10 124.42(19) . . ?
N2 C1 Cl11 116.57(16) . . ?
C10 C1 Cl11 119.02(16) . . ?
F13 C12 C10 108.30(16) . . ?
F13 C12 H12A 110.0 . . ?
C10 C12 H12A 110.0 . . ?
F13 C12 H12B 110.0 . . ?
C10 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?

_refine_diff_density_max         0.717
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_rkn_925
_database_code_depnum_ccdc_archive 'CCDC 2277851'
loop_
_audit_author_name
_audit_author_address
'Anatoly Mishnev'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 F4 N2 O'
_chemical_formula_sum            'C11 H8 F4 N2 O'
_chemical_formula_weight         260.19

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.4989(2)
_cell_length_b                   7.09040(10)
_cell_length_c                   20.0236(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2058.49(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6479
_cell_measurement_theta_min      5.3570
_cell_measurement_theta_max      76.4180

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.413
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10196
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.416
_diffrn_reflns_theta_max         76.488
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2078
_reflns_number_gt                1840
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.7159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2078
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
F12 F 0.10908(6) 0.54295(13) 0.76461(4) 0.0341(2) Uani 1 1 d . . . . .
F13 F 0.08832(7) 0.24603(14) 0.75734(5) 0.0419(3) Uani 1 1 d . . . . .
F16 F 0.21219(6) 0.11814(17) 0.38024(5) 0.0470(3) Uani 1 1 d . . . . .
F14 F 0.02409(6) 0.43109(19) 0.68656(5) 0.0492(3) Uani 1 1 d . . . . .
O17 O 0.47106(7) 0.1999(2) 0.45472(5) 0.0393(3) Uani 1 1 d . . . . .
N7 N 0.41686(7) 0.29198(17) 0.55689(6) 0.0229(3) Uani 1 1 d . . . . .
N4 N 0.23792(7) 0.23746(17) 0.50514(5) 0.0220(3) Uani 1 1 d . . . . .
C8 C 0.34068(8) 0.32450(18) 0.59755(6) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.18449(9) 0.38362(18) 0.67619(6) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.34982(9) 0.38219(19) 0.66417(7) 0.0223(3) Uani 1 1 d . . . . .
H9 H 0.409395 0.401813 0.682654 0.027 Uiso 1 1 calc R U . . .
C3 C 0.25174(9) 0.29733(19) 0.57069(6) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.17399(8) 0.32804(19) 0.61034(6) 0.0201(3) Uani 1 1 d . . . . .
H2 H 0.114033 0.310841 0.592199 0.024 Uiso 1 1 calc R U . . .
C10 C 0.27257(9) 0.41044(19) 0.70283(7) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.279209 0.448529 0.748063 0.027 Uiso 1 1 calc R U . . .
C5 C 0.31028(9) 0.2056(2) 0.46986(7) 0.0232(3) Uani 1 1 d . . . . .
C6 C 0.40649(9) 0.2310(2) 0.49252(7) 0.0256(3) Uani 1 1 d . . . . .
C11 C 0.10180(9) 0.4019(2) 0.72041(7) 0.0251(3) Uani 1 1 d . . . . .
C18 C 0.51083(9) 0.3224(3) 0.58247(8) 0.0321(4) Uani 1 1 d . . . . .
H18A H 0.555475 0.301228 0.546496 0.038 Uiso 1 1 calc R U . . .
H18B H 0.522988 0.234217 0.619099 0.038 Uiso 1 1 calc R U . . .
H18C H 0.516610 0.452157 0.598835 0.038 Uiso 1 1 calc R U . . .
C15 C 0.30339(10) 0.1370(3) 0.39892(7) 0.0315(3) Uani 1 1 d . . . . .
H15A H 0.334505 0.227737 0.368830 0.038 Uiso 1 1 calc R U . . .
H15B H 0.334989 0.013824 0.394712 0.038 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
F12 C11 1.3395(17) . ?
F13 C11 1.3442(17) . ?
F16 C15 1.3808(16) . ?
F14 C11 1.3311(16) . ?
O17 C6 1.2239(17) . ?
N7 C6 1.3679(18) . ?
N7 C8 1.3914(16) . ?
N7 C18 1.4714(16) . ?
N4 C5 1.2850(17) . ?
N4 C3 1.3939(16) . ?
C8 C9 1.4015(19) . ?
C8 C3 1.4105(17) . ?
C1 C2 1.3845(18) . ?
C1 C10 1.3970(18) . ?
C1 C11 1.4961(18) . ?
C9 C10 1.3761(19) . ?
C9 H9 0.9500 . ?
C3 C2 1.3959(17) . ?
C2 H2 0.9500 . ?
C10 H10 0.9500 . ?
C5 C6 1.4778(18) . ?
C5 C15 1.5046(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C6 N7 C8 121.10(11) . . ?
C6 N7 C18 118.43(11) . . ?
C8 N7 C18 120.47(11) . . ?
C5 N4 C3 116.99(11) . . ?
N7 C8 C9 122.02(11) . . ?
N7 C8 C3 118.69(11) . . ?
C9 C8 C3 119.29(11) . . ?
C2 C1 C10 120.19(12) . . ?
C2 C1 C11 120.01(12) . . ?
C10 C1 C11 119.65(12) . . ?
C10 C9 C8 120.06(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N4 C3 C2 117.84(11) . . ?
N4 C3 C8 122.15(11) . . ?
C2 C3 C8 120.00(11) . . ?
C1 C2 C3 119.82(11) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C9 C10 C1 120.62(12) . . ?
C9 C10 H10 119.7 . . ?
C1 C10 H10 119.7 . . ?
N4 C5 C6 125.48(12) . . ?
N4 C5 C15 121.44(12) . . ?
C6 C5 C15 113.07(11) . . ?
O17 C6 N7 123.74(12) . . ?
O17 C6 C5 120.68(13) . . ?
N7 C6 C5 115.57(11) . . ?
F14 C11 F12 106.68(11) . . ?
F14 C11 F13 106.55(12) . . ?
F12 C11 F13 105.18(11) . . ?
F14 C11 C1 112.98(12) . . ?
F12 C11 C1 113.12(11) . . ?
F13 C11 C1 111.77(11) . . ?
N7 C18 H18A 109.5 . . ?
N7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F16 C15 C5 110.53(11) . . ?
F16 C15 H15A 109.5 . . ?
C5 C15 H15A 109.5 . . ?
F16 C15 H15B 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.048

