# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_2Bcr-m28
_database_code_depnum_ccdc_archive 'CCDC 2118100'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
4-amino-2,3,6-trifluorobenzonitrile 18-crown-6 associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          432
_chemical_formula_moiety         '2(C7 H3 F3 N2), C12 H24 O6'
_chemical_formula_sum            'C26 H30 F6 N4 O6'
_chemical_formula_weight         608.54

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.4786(6)
_cell_length_b                   11.6381(6)
_cell_length_c                   34.8047(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.017(3)
_cell_angle_gamma                90
_cell_volume                     5864.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5750
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      21.70

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             2528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8633
_exptl_absorpt_correction_T_max  0.9561
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16444
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         0.585
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5311
_reflns_number_gt                2751
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5311
_refine_ls_number_parameters     378
_refine_ls_number_restraints     546
_refine_ls_R_factor_all          0.1868
_refine_ls_R_factor_gt           0.1302
_refine_ls_wR_factor_ref         0.4345
_refine_ls_wR_factor_gt          0.3871
_refine_ls_goodness_of_fit_ref   1.482
_refine_ls_restrained_S_all      1.492
_refine_ls_shift/su_max          0.078
_refine_ls_shift/su_mean         0.020

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
N1 N 0.9950(5) 0.7486(5) 0.09189(15) 0.0732(14) Uani 1 1 d . U . . .
H1 H 1.044692 0.729984 0.103937 0.088 Uiso 1 1 calc R U . . .
H2 H 0.942202 0.740676 0.102875 0.088 Uiso 1 1 calc R U . . .
F1 F 1.1661(5) 0.8631(8) -0.0170(2) 0.157(3) Uani 1 1 d . U . . .
C1 C 1.0008(10) 0.8628(6) -0.0211(2) 0.102(2) Uani 1 1 d D U . . .
F2 F 1.1594(11) 0.7972(14) 0.0528(4) 0.142(5) Uiso 0.5 1 d . U P . .
F2A F 0.8397(8) 0.7989(10) 0.0533(3) 0.108(3) Uiso 0.5 1 d . U P . .
C2 C 1.0792(8) 0.8470(9) -0.0018(3) 0.099(3) Uani 1 1 d . U . . .
N2 N 1.011(2) 0.9268(13) -0.0915(3) 0.253(9) Uani 1 1 d D U . . .
C3 C 1.0818(5) 0.8045(7) 0.0370(2) 0.0717(19) Uani 1 1 d . U . . .
H3A H 1.139740 0.786260 0.049080 0.086 Uiso 0.5 1 d . U P . .
F3 F 0.8433(5) 0.8702(7) -0.0186(2) 0.153(3) Uani 1 1 d . U . . .
C4 C 0.9999(7) 0.7897(6) 0.05622(19) 0.085(2) Uani 1 1 d . U . . .
C5 C 0.9185(8) 0.8110(9) 0.0357(3) 0.097(3) Uani 1 1 d . U . . .
H5A H 0.860460 0.801480 0.049160 0.117 Uiso 0.5 1 d . U P . .
C6 C 0.9155(9) 0.8423(9) 0.0002(3) 0.098(3) Uani 1 1 d . U . . .
C7 C 0.9980(10) 0.8865(8) -0.0608(2) 0.122(4) Uani 1 1 d D U . . .
N3 N 1.0027(6) 0.5482(5) 0.16506(16) 0.0870(17) Uani 1 1 d . U . . .
H3 H 0.980461 0.614238 0.171143 0.104 Uiso 1 1 calc R U . . .
H4 H 1.040765 0.542184 0.146214 0.104 Uiso 1 1 calc R U . . .
F4 F 0.8308(7) 0.3886(6) 0.2629(3) 0.166(3) Uani 1 1 d . U . . .
N4 N 0.8342(6) 0.0833(6) 0.2524(4) 0.140(3) Uani 1 1 d D U . . .
F5 F 0.8987(8) 0.5796(10) 0.2311(3) 0.114(3) Uiso 0.5 1 d . U P . .
F5A F 1.0505(10) 0.3274(13) 0.1440(4) 0.137(4) Uiso 0.5 1 d . U P . .
F6 F 1.0075(8) 0.1470(3) 0.18023(19) 0.160(3) Uani 1 1 d . U . . .
C8 C 0.8997(7) 0.2700(8) 0.2235(3) 0.101(3) Uani 1 1 d D U . . .
C9 C 0.8622(9) 0.3852(8) 0.2337(2) 0.102(3) Uani 1 1 d . U . . .
C10 C 0.9188(6) 0.4678(7) 0.2139(2) 0.086(2) Uani 1 1 d . U . . .
H10A H 0.913290 0.544820 0.223930 0.104 Uiso 0.5 1 d . U P . .
C11 C 0.9791(9) 0.4588(6) 0.1840(2) 0.099(3) Uani 1 1 d . U . . .
C12 C 0.9942(6) 0.3460(4) 0.17227(17) 0.0680(16) Uani 1 1 d . U . . .
H12A H 1.031120 0.330230 0.149710 0.082 Uiso 0.5 1 d . U P . .
C13 C 0.9576(6) 0.2595(7) 0.1932(3) 0.090(2) Uani 1 1 d . U . . .
C14 C 0.8637(6) 0.1700(8) 0.2460(4) 0.113(3) Uani 1 1 d D U . . .
O1 O 0.8321(6) 0.7304(10) 0.1443(3) 0.171(4) Uani 1 1 d D U . . .
O2 O 0.8376(9) 0.5312(13) 0.1008(4) 0.205(6) Uani 1 1 d D U . . .
O3 O 1.0134(10) 0.4846(11) 0.0625(4) 0.206(5) Uani 1 1 d D U . . .
O4 O 1.1644(8) 0.5505(12) 0.1046(4) 0.241(7) Uani 1 1 d D U . . .
O5 O 1.1578(8) 0.7412(11) 0.1519(3) 0.208(6) Uani 1 1 d D U . . .
O6 O 0.9927(9) 0.8007(5) 0.18194(19) 0.166(4) Uani 1 1 d D U . . .
C15 C 0.7595(8) 0.6523(14) 0.1435(4) 0.172(7) Uani 1 1 d D U . . .
H15A H 0.701315 0.691899 0.147267 0.207 Uiso 1 1 calc R U . . .
H15B H 0.766888 0.596206 0.163897 0.207 Uiso 1 1 calc R U . . .
C16 C 0.7602(9) 0.5962(16) 0.1070(5) 0.222(8) Uani 1 1 d D U . . .
H16A H 0.706221 0.547200 0.105089 0.266 Uiso 1 1 calc R U . . .
H16B H 0.755721 0.653890 0.086944 0.266 Uiso 1 1 calc R U . . .
C17 C 0.8548(10) 0.4712(16) 0.0681(6) 0.197(7) Uani 1 1 d D U . . .
H17A H 0.860364 0.521380 0.045923 0.236 Uiso 1 1 calc R U . . .
H17B H 0.807669 0.413784 0.063182 0.236 Uiso 1 1 calc R U . . .
C18 C 0.9456(13) 0.417(2) 0.0786(8) 0.264(10) Uani 1 1 d D U . . .
H18A H 0.952649 0.414789 0.106261 0.317 Uiso 1 1 calc R U . . .
H18B H 0.949070 0.339703 0.068632 0.317 Uiso 1 1 calc R U . . .
C19 C 1.0965(12) 0.4305(15) 0.0611(4) 0.190(7) Uani 1 1 d D U . . .
H19A H 1.103358 0.395885 0.035931 0.228 Uiso 1 1 calc R U . . .
H19B H 1.096065 0.368687 0.079828 0.228 Uiso 1 1 calc R U . . .
C20 C 1.1753(12) 0.5013(18) 0.0683(6) 0.237(9) Uani 1 1 d D U . . .
H20A H 1.231226 0.455550 0.067525 0.284 Uiso 1 1 calc R U . . .
H20B H 1.179796 0.560926 0.048914 0.284 Uiso 1 1 calc R U . . .
C21 C 1.2367(9) 0.6254(17) 0.1146(5) 0.225(9) Uani 1 1 d D U . . .
H21A H 1.234752 0.694244 0.098889 0.269 Uiso 1 1 calc R U . . .
H21B H 1.296070 0.588282 0.111035 0.269 Uiso 1 1 calc R U . . .
C22 C 1.2221(12) 0.6528(16) 0.1541(5) 0.222(9) Uani 1 1 d D U . . .
H22A H 1.197703 0.587516 0.168124 0.267 Uiso 1 1 calc R U . . .
H22B H 1.278794 0.678367 0.166256 0.267 Uiso 1 1 calc R U . . .
C23 C 1.1532(9) 0.8131(14) 0.1825(5) 0.203(8) Uani 1 1 d D U . . .
H23A H 1.203519 0.868001 0.181385 0.244 Uiso 1 1 calc R U . . .
H23B H 1.159326 0.769392 0.206123 0.244 Uiso 1 1 calc R U . . .
C24 C 1.0653(11) 0.8740(8) 0.1825(3) 0.176(7) Uani 1 1 d D U . . .
H24A H 1.061452 0.921992 0.205253 0.211 Uiso 1 1 calc R U . . .
H24B H 1.062302 0.923786 0.160184 0.211 Uiso 1 1 calc R U . . .
C25 C 0.9064(12) 0.8667(13) 0.1813(5) 0.192(7) Uani 1 1 d D U . . .
H25A H 0.900876 0.911769 0.157923 0.230 Uiso 1 1 calc R U . . .
H25B H 0.901476 0.917110 0.203365 0.230 Uiso 1 1 calc R U . . .
C26 C 0.8363(10) 0.7724(17) 0.1827(5) 0.197(7) Uani 1 1 d D U . . .
H26A H 0.855389 0.712303 0.200235 0.236 Uiso 1 1 calc R U . . .
H26B H 0.776656 0.801728 0.190752 0.236 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
N1 C4 1.332(9) . ?
F1 C2 1.379(13) . ?
C1 C2 1.333(15) . ?
C1 C7 1.410(10) . ?
C1 C6 1.461(17) . ?
F2 C3 1.254(16) . ?
F2A C5 1.303(14) . ?
C2 C3 1.437(13) . ?
N2 C7 1.183(12) . ?
C3 C4 1.373(11) . ?
F3 C6 1.275(12) . ?
C4 C5 1.400(14) . ?
C5 C6 1.288(13) . ?
N3 C11 1.279(9) . ?
F4 C9 1.114(10) . ?
N4 C14 1.118(9) . ?
F5 C10 1.461(15) . ?
F5A C12 1.297(16) . ?
F6 C13 1.562(11) . ?
C8 C13 1.352(13) . ?
C8 C9 1.490(15) . ?
C8 C14 1.496(10) . ?
C9 C10 1.440(13) . ?
C10 C11 1.361(13) . ?
C11 C12 1.393(9) . ?
C12 C13 1.350(11) . ?
O1 C15 1.390(13) . ?
O1 C26 1.424(14) . ?
O2 C17 1.359(15) . ?
O2 C16 1.370(15) . ?
O3 C19 1.358(15) . ?
O3 C18 1.374(17) . ?
O4 C20 1.396(15) . ?
O4 C21 1.405(15) . ?
O5 C23 1.356(14) . ?
O5 C22 1.389(14) . ?
O6 C24 1.354(13) . ?
O6 C25 1.467(14) . ?
C15 C16 1.428(15) . ?
C17 C18 1.501(17) . ?
C19 C20 1.430(15) . ?
C21 C22 1.428(16) . ?
C23 C24 1.456(15) . ?
C25 C26 1.496(16) . ?

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
C2 C1 C7 123.1(12) . . ?
C2 C1 C6 116.2(7) . . ?
C7 C1 C6 120.4(12) . . ?
C1 C2 F1 124.4(9) . . ?
C1 C2 C3 122.9(9) . . ?
F1 C2 C3 112.6(9) . . ?
F2 C3 C4 123.5(9) . . ?
F2 C3 C2 117.3(10) . . ?
C4 C3 C2 118.6(8) . . ?
N1 C4 C3 123.1(9) . . ?
N1 C4 C5 119.6(8) . . ?
C3 C4 C5 117.1(6) . . ?
F2A C5 C6 116.9(11) . . ?
F2A C5 C4 118.5(9) . . ?
C6 C5 C4 124.6(10) . . ?
F3 C6 C5 126.3(12) . . ?
F3 C6 C1 112.9(9) . . ?
C5 C6 C1 120.3(11) . . ?
N2 C7 C1 163.5(14) . . ?
C13 C8 C9 119.6(8) . . ?
C13 C8 C14 123.6(10) . . ?
C9 C8 C14 116.6(9) . . ?
F4 C9 C10 130.2(10) . . ?
F4 C9 C8 113.6(8) . . ?
C10 C9 C8 106.1(9) . . ?
C11 C10 F5 120.6(8) . . ?
C11 C10 C9 132.8(8) . . ?
F5 C10 C9 106.6(8) . . ?
N3 C11 C10 120.2(8) . . ?
N3 C11 C12 124.9(8) . . ?
C10 C11 C12 113.5(7) . . ?
F5A C12 C13 122.2(9) . . ?
F5A C12 C11 118.7(9) . . ?
C13 C12 C11 118.8(8) . . ?
C8 C13 C12 126.6(8) . . ?
C8 C13 F6 126.0(8) . . ?
C12 C13 F6 106.7(7) . . ?
N4 C14 C8 160.0(15) . . ?
C15 O1 C26 105.9(10) . . ?
C17 O2 C16 124.5(12) . . ?
C19 O3 C18 112.5(15) . . ?
C20 O4 C21 113.2(12) . . ?
C23 O5 C22 116.6(11) . . ?
C24 O6 C25 109.3(8) . . ?
O1 C15 C16 108.1(11) . . ?
O2 C16 C15 113.5(13) . . ?
O2 C17 C18 99.8(16) . . ?
O3 C18 C17 106.8(17) . . ?
O3 C19 C20 115.7(14) . . ?
O4 C20 C19 107.7(12) . . ?
O4 C21 C22 105.4(12) . . ?
O5 C22 C21 102.3(13) . . ?
O5 C23 C24 110.1(9) . . ?
O6 C24 C23 111.8(10) . . ?
O6 C25 C26 101.2(11) . . ?
O1 C26 C25 104.5(12) . . ?

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.125


####################################################################### 
# 
# 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_E-M909_2
_database_code_depnum_ccdc_archive 'CCDC 2118107'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        2-amino-4-chloro-3,6-difluorobenzonitrile
_chemical_name_common            ?
_chemical_melting_point          379
_chemical_formula_moiety         'C7 H2 Cl F2 N2'
_chemical_formula_sum            'C7 H2 Cl F2 N2'
_chemical_formula_weight         187.56

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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                   7.6581(3)
_cell_length_b                   7.3941(3)
_cell_length_c                   13.4241(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.090(2)
_cell_angle_gamma                90
_cell_volume                     752.57(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3904
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.87

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.479
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8330
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7523
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.686
_diffrn_reflns_theta_max         27.900
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1792
_reflns_number_gt                1445
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0577P)²+0.2371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1792
_refine_ls_number_parameters     117
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
Cl1 Cl 0.42221(8) -0.39061(7) 0.12353(5) 0.0665(2) Uani 1 1 d . . . . .
F1 F 0.27829(17) -0.09466(16) 0.22757(8) 0.0601(3) Uani 1 1 d . . . . .
C1 C 0.1948(2) 0.1254(2) -0.01440(12) 0.0374(4) Uani 1 1 d . . . . .
N1 N 0.1402(3) 0.2197(2) 0.15185(12) 0.0579(5) Uani 1 1 d D . . . .
H1 H 0.092(3) 0.322(3) 0.1304(19) 0.070(7) Uiso 1 1 d D . . . .
H2 H 0.144(3) 0.189(4) 0.2153(14) 0.076(7) Uiso 1 1 d D . . . .
F2 F 0.2458(2) 0.02211(19) -0.17154(8) 0.0733(4) Uani 1 1 d . . . . .
C2 C 0.2008(2) 0.0982(2) 0.08994(12) 0.0369(4) Uani 1 1 d . . . . .
N2 N 0.0668(2) 0.4161(2) -0.10007(14) 0.0592(5) Uani 1 1 d . . . . .
C3 C 0.2732(2) -0.0661(2) 0.12843(12) 0.0397(4) Uani 1 1 d . . . . .
C4 C 0.3341(2) -0.1947(2) 0.06878(13) 0.0424(4) Uani 1 1 d . . . . .
C5 C 0.3261(3) -0.1695(3) -0.03420(14) 0.0499(4) Uani 1 1 d . . . . .
H5 H 0.366089 -0.257121 -0.075258 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2568(2) -0.0103(3) -0.07211(12) 0.0457(4) Uani 1 1 d . . . . .
C7 C 0.1241(2) 0.2877(2) -0.06159(13) 0.0429(4) Uani 1 1 d . . . . .


_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
Cl1 C4 1.7187(17) . ?
F1 C3 1.3426(19) . ?
C1 C6 1.391(2) . ?
C1 C2 1.409(2) . ?
C1 C7 1.428(2) . ?
N1 C2 1.349(2) . ?
N1 H1 0.874(17) . ?
N1 H2 0.878(17) . ?
F2 C6 1.3470(19) . ?
C2 C3 1.404(2) . ?
N2 C7 1.139(2) . ?
C3 C4 1.367(2) . ?
C4 C5 1.388(2) . ?
C5 C6 1.360(3) . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.01(15) . . ?
C6 C1 C7 119.80(15) . . ?
C2 C1 C7 121.18(15) . . ?
C2 N1 H1 122.7(17) . . ?
C2 N1 H2 117.5(18) . . ?
H1 N1 H2 120(2) . . ?
N1 C2 C3 120.10(15) . . ?
N1 C2 C1 123.47(15) . . ?
C3 C2 C1 116.42(14) . . ?
F1 C3 C4 120.42(15) . . ?
F1 C3 C2 117.13(15) . . ?
C4 C3 C2 122.44(15) . . ?
C3 C4 C5 121.28(16) . . ?
C3 C4 Cl1 118.80(13) . . ?
C5 C4 Cl1 119.92(14) . . ?
C6 C5 C4 116.69(16) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
F2 C6 C5 119.43(16) . . ?
F2 C6 C1 116.41(16) . . ?
C5 C6 C1 124.15(16) . . ?
N2 C7 C1 179.3(2) . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.055




####################################################################### 
# 
# 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_D-Mal1275
_database_code_depnum_ccdc_archive 'CCDC 2118106'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        2-amino-4-chloro-3,5,6-trifluorobenzonitrile
_chemical_name_common            ?
_chemical_melting_point          396
_chemical_formula_moiety         'C7 H2 Cl F3 N2'
_chemical_formula_sum            'C7 H2 Cl F3 N2'
_chemical_formula_weight         206.56

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.7777(19)
_cell_length_b                   7.7816(15)
_cell_length_c                   10.2460(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.955(8)
_cell_angle_gamma                90
_cell_volume                     767.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2405
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      26.08

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.380
_exptl_absorpt_coefficient_mu    0.497
_shelx_estimated_absorpt_T_min   0.735
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5694
_exptl_absorpt_correction_T_max  0.6938
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3105
_diffrn_reflns_av_unetI/netI     0.1039
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.366
_diffrn_reflns_theta_max         26.145
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             799
_reflns_number_gt                505
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0039P)²+14.9187P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         799
_refine_ls_number_parameters     67
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0962
_refine_ls_wR_factor_ref         0.2820
_refine_ls_wR_factor_gt          0.2726
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Cl1 Cl 0.7297(3) 0.500000 0.0485(3) 0.0722(12) Uani 1 2 d S T P . .
F1 F 0.4245(7) 0.1984(8) 0.3244(7) 0.086(2) Uani 0.5 1 d . . P . .
N1 N 0.4245(7) 0.1984(8) 0.3244(7) 0.086(2) Uani 0.5 1 d . . P . .
H1 H 0.454091 0.102620 0.297976 0.103 Uiso 0.5 1 calc R U P . .
H2 H 0.365147 0.198512 0.377337 0.103 Uiso 0.5 1 calc R U P . .
C1 C 0.4234(10) 0.500000 0.3262(10) 0.043(2) Uani 1 2 d S T P . .
N2 N 0.2401(13) 0.500000 0.4758(13) 0.108(5) Uani 1 2 d S T P . .
F2 F 0.6119(6) 0.1966(6) 0.1592(5) 0.0732(17) Uani 1 1 d . . . . .
C2 C 0.4710(8) 0.3478(11) 0.2830(7) 0.053(2) Uani 1 1 d . . . . .
C3 C 0.5653(7) 0.3500(8) 0.1989(7) 0.0422(17) Uani 1 1 d . . . . .
C4 C 0.6147(10) 0.500000 0.1559(9) 0.039(2) Uani 1 2 d S T P . .
C5 C 0.3196(11) 0.500000 0.4108(11) 0.058(3) Uani 1 2 d S T P . .


_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
Cl1 C4 1.704(9) . ?
F1 C2 1.344(9) . ?
C1 C2 1.373(9) 6_565 ?
C1 C2 1.373(9) . ?
C1 C5 1.444(14) . ?
N2 C5 1.107(15) . ?
F2 C3 1.365(8) . ?
C2 C3 1.367(10) . ?
C3 C4 1.365(8) . ?

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
C2 C1 C2 119.2(9) 6_565 . ?
C2 C1 C5 120.4(4) 6_565 . ?
C2 C1 C5 120.4(4) . . ?
F1 C2 C3 120.8(7) . . ?
F1 C2 C1 119.5(7) . . ?
C3 C2 C1 119.7(7) . . ?
F2 C3 C4 119.8(6) . . ?
F2 C3 C2 118.3(6) . . ?
C4 C3 C2 121.9(7) . . ?
C3 C4 C3 117.5(9) . 6_565 ?
C3 C4 Cl1 121.2(4) . . ?
C3 C4 Cl1 121.2(4) 6_565 . ?
N2 C5 C1 179.9(13) . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.093


####################################################################### 
# 
# 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_B-M98
_database_code_depnum_ccdc_archive 'CCDC 2118104'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        4-amino-2,3,6-trifluorobenzonitrile
_chemical_name_common            ?
_chemical_melting_point          367
_chemical_formula_moiety         'C7 H3 F3 N2'
_chemical_formula_sum            'C7 H3 F3 N2'
_chemical_formula_weight         172.11

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'
N N 0.0061 0.0033 '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'

_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                   7.5702(5)
_cell_length_b                   5.8303(3)
_cell_length_c                   15.8912(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.846(3)
_cell_angle_gamma                90
_cell_volume                     696.38(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3475
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.18

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8518
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7627
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.582
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1587
_reflns_number_gt                1084
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0536P)²+0.4947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1587
_refine_ls_number_parameters     117
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
N1 N 0.1954(3) 0.7122(4) -0.04119(14) 0.0601(6) Uani 1 1 d D . . . .
H2 H 0.126(4) 0.838(4) -0.042(2) 0.090(11) Uiso 1 1 d D . . . .
H1 H 0.237(4) 0.652(5) -0.0874(14) 0.079(9) Uiso 1 1 d D . . . .
F1 F 0.1179(2) 0.6271(3) 0.24816(9) 0.0683(5) Uani 1 1 d . . . . .
C1 C 0.2740(3) 0.3394(4) 0.18427(14) 0.0443(5) Uani 1 1 d . . . . .
F2 F 0.0639(2) 0.8648(3) 0.10155(10) 0.0658(5) Uani 1 1 d . . . . .
N2 N 0.3198(4) 0.1005(5) 0.32108(15) 0.0786(8) Uani 1 1 d . . . . .
C2 C 0.1821(3) 0.5452(4) 0.17898(13) 0.0448(5) Uani 1 1 d . . . . .
C3 C 0.1559(3) 0.6649(4) 0.10457(14) 0.0447(5) Uani 1 1 d . . . . .
F3 F 0.4301(2) 0.0658(3) 0.11504(10) 0.0694(5) Uani 1 1 d . . . . .
C4 C 0.2210(3) 0.5873(4) 0.03148(14) 0.0439(5) Uani 1 1 d . . . . .
C5 C 0.3138(3) 0.3791(4) 0.03593(14) 0.0469(5) Uani 1 1 d . . . . .
H5 H 0.358432 0.320379 -0.011676 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3377(3) 0.2641(4) 0.11077(15) 0.0474(5) Uani 1 1 d . . . . .
C7 C 0.3001(3) 0.2096(5) 0.26080(17) 0.0563(6) Uani 1 1 d . . . . .


_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
N1 C4 1.360(3) . ?
N1 H2 0.898(18) . ?
N1 H1 0.903(17) . ?
F1 C2 1.342(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.387(3) . ?
C1 C7 1.426(3) . ?
F2 C3 1.355(2) . ?
N2 C7 1.145(3) . ?
C2 C3 1.367(3) . ?
C3 C4 1.390(3) . ?
F3 C6 1.349(3) . ?
C4 C5 1.400(3) . ?
C5 C6 1.358(3) . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 H2 118(2) . . ?
C4 N1 H1 117(2) . . ?
H2 N1 H1 124(3) . . ?
C2 C1 C6 116.5(2) . . ?
C2 C1 C7 121.9(2) . . ?
C6 C1 C7 121.6(2) . . ?
F1 C2 C3 119.9(2) . . ?
F1 C2 C1 119.2(2) . . ?
C3 C2 C1 121.0(2) . . ?
F2 C3 C2 119.37(19) . . ?
F2 C3 C4 118.8(2) . . ?
C2 C3 C4 121.8(2) . . ?
N1 C4 C3 120.4(2) . . ?
N1 C4 C5 121.8(2) . . ?
C3 C4 C5 117.7(2) . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
F3 C6 C5 118.8(2) . . ?
F3 C6 C1 117.3(2) . . ?
C5 C6 C1 123.9(2) . . ?
N2 C7 C1 178.3(3) . . ?

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
C6 C1 C2 F1 -179.71(19) . . . . ?
C7 C1 C2 F1 1.1(3) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C7 C1 C2 C3 -178.9(2) . . . . ?
F1 C2 C3 F2 -0.5(3) . . . . ?
C1 C2 C3 F2 179.44(19) . . . . ?
F1 C2 C3 C4 179.57(19) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
F2 C3 C4 N1 1.2(3) . . . . ?
C2 C3 C4 N1 -178.9(2) . . . . ?
F2 C3 C4 C5 -179.31(18) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
N1 C4 C5 C6 178.8(2) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 F3 -178.80(19) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 F3 178.97(18) . . . . ?
C7 C1 C6 F3 -1.8(3) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 178.8(2) . . . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.040


####################################################################### 
# 
# 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_2Ccr-m27
_database_code_depnum_ccdc_archive 'CCDC 2118101'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
4-amino-2,3,5-trifluorobenzonitrile 18-crown-6 associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          403
_chemical_formula_moiety         '2(C7 H3 F3 N2), C12 H24 O6'
_chemical_formula_sum            'C26 H30 F6 N4 O6'
_chemical_formula_weight         608.54

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.4590(6)
_cell_length_b                   11.6131(6)
_cell_length_c                   34.7535(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.333(3)
_cell_angle_gamma                90
_cell_volume                     5835.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9383
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      22.91

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             2528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8960
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24213
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.172
_diffrn_reflns_theta_max         25.788
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5505
_reflns_number_gt                3834
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1989P)²+7.6800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5505
_refine_ls_number_parameters     385
_refine_ls_number_restraints     673
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.2939
_refine_ls_wR_factor_gt          0.2544
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
N1 N 0.9755(3) 0.7743(4) 0.08908(11) 0.0729(11) Uani 1 1 d . . . . .
H2 H 0.923514 0.760595 0.100039 0.087 Uiso 1 1 calc R U . . .
H1 H 1.026191 0.769591 0.102078 0.087 Uiso 1 1 calc R U . . .
F1 F 1.1479(3) 0.8764(4) -0.02005(11) 0.1075(12) Uani 1 1 d . U . . .
C1 C 0.9883(4) 0.8634(4) -0.02748(13) 0.0650(12) Uani 1 1 d . U . . .
F2 F 1.1395(2) 0.8216(4) 0.05455(10) 0.1005(11) Uani 1 1 d . U . . .
N2 N 1.0014(5) 0.9128(5) -0.09931(16) 0.1106(19) Uani 1 1 d . U . . .
C2 C 1.0657(4) 0.8561(4) -0.00495(14) 0.0663(12) Uani 1 1 d . U . . .
C3 C 1.0617(3) 0.8271(4) 0.03321(13) 0.0629(11) Uani 1 1 d . U . . .
F3 F 0.8174(2) 0.7923(4) 0.04421(11) 0.1006(11) Uani 1 1 d . U . . .
C4 C 0.9777(3) 0.8030(3) 0.05157(12) 0.0595(11) Uani 1 1 d . U . . .
C5 C 0.9011(3) 0.8131(4) 0.02785(14) 0.0641(11) Uani 1 1 d . U . . .
C6 C 0.9034(4) 0.8415(4) -0.00987(16) 0.0743(13) Uani 1 1 d . U . . .
H6 H 0.848737 0.846304 -0.024041 0.089 Uiso 1 1 calc R U . . .
C7 C 0.9945(5) 0.8919(5) -0.06726(15) 0.0814(15) Uani 1 1 d . U . . .
N3 N 1.0039(3) 0.5587(3) 0.16669(12) 0.0725(11) Uani 1 1 d . U . A 1
H4 H 0.988422 0.626641 0.174104 0.087 Uiso 1 1 calc R U . A 1
H3 H 1.040243 0.550205 0.147399 0.087 Uiso 1 1 calc R U . A 1
N4 N 0.8414(4) 0.0912(4) 0.25806(18) 0.1002(17) Uani 1 1 d . U . A 1
F5 F 0.8916(3) 0.5819(2) 0.22935(10) 0.0879(10) Uani 1 1 d . U . A 1
F6 F 1.0510(3) 0.3424(3) 0.14417(10) 0.0933(10) Uani 1 1 d . U . A 1
C8 C 0.9010(3) 0.2710(4) 0.22305(13) 0.0598(10) Uani 1 1 d . U . A 1
C9 C 0.8776(3) 0.3807(4) 0.23471(12) 0.0599(11) Uani 1 1 d . U . A 1
H13A H 0.837474 0.390534 0.255274 0.072 Uiso 0.225(10) 1 calc R U P B 1
C10 C 0.9126(3) 0.4750(4) 0.21640(12) 0.0575(10) Uani 1 1 d . U . A 1
C11 C 0.9718(3) 0.4676(4) 0.18488(12) 0.0581(10) Uani 1 1 d . U . A 1
C12 C 0.9922(3) 0.3531(4) 0.17379(12) 0.0553(10) Uani 1 1 d . U . A 1
C13 C 0.9594(3) 0.2596(4) 0.19173(14) 0.0646(11) Uani 0.9 1 d . U P A 1
H13 H 0.975789 0.186662 0.183133 0.077 Uiso 0.775(10) 1 calc R U P B 1
C14 C 0.8663(4) 0.1725(4) 0.24366(16) 0.0739(13) Uani 1 1 d . U . A 1
F4 F 0.8254(3) 0.3924(3) 0.26449(12) 0.0868(16) Uani 0.775(10) 1 d . U P B 2
C13A C 0.9594(3) 0.2596(4) 0.19173(14) 0.0646(11) Uani 0.1 1 d D U P B 2
F4A F 0.9766(12) 0.1579(12) 0.1845(5) 0.094(6) Uiso 0.225(10) 1 d D U P B 2
O1 O 0.9582(3) 0.8130(3) 0.18069(10) 0.0786(10) Uani 1 1 d D U . . .
O2 O 0.8117(3) 0.7153(4) 0.13921(11) 0.0874(11) Uani 1 1 d D U . . .
O3 O 0.8392(5) 0.5230(7) 0.0937(2) 0.169(3) Uani 1 1 d D U . . .
O4 O 1.0142(5) 0.5023(5) 0.0603(2) 0.149(2) Uani 1 1 d D U . . .
O5 O 1.1613(4) 0.5709(4) 0.10674(16) 0.1170(16) Uani 1 1 d D U . . .
O6 O 1.1389(3) 0.7702(4) 0.15241(12) 0.0881(11) Uani 1 1 d D U . . .
C15 C 0.8728(5) 0.8724(5) 0.17371(17) 0.0897(16) Uani 1 1 d D U . . .
H15A H 0.876951 0.916270 0.150039 0.108 Uiso 1 1 calc R U . . .
H15B H 0.860651 0.925519 0.194616 0.108 Uiso 1 1 calc R U . . .
C16 C 0.7979(4) 0.7888(6) 0.17073(17) 0.0934(17) Uani 1 1 d D U . . .
H16A H 0.795083 0.743738 0.194189 0.112 Uiso 1 1 calc R U . . .
H16B H 0.739468 0.828955 0.167681 0.112 Uiso 1 1 calc R U . . .
C17 C 0.7477(4) 0.6240(6) 0.1372(2) 0.1001(19) Uani 1 1 d D U . . .
H17A H 0.685823 0.655889 0.135336 0.120 Uiso 1 1 calc R U . . .
H17B H 0.751296 0.580235 0.160970 0.120 Uiso 1 1 calc R U . . .
C18 C 0.7617(6) 0.5484(8) 0.1060(3) 0.136(3) Uani 1 1 d D U . . .
H18A H 0.731696 0.476511 0.112666 0.163 Uiso 1 1 calc R U . . .
H18B H 0.727363 0.580109 0.084380 0.163 Uiso 1 1 calc R U . . .
C19 C 0.8544(7) 0.4750(9) 0.0588(3) 0.163(4) Uani 1 1 d D U . . .
H19A H 0.842989 0.533044 0.039282 0.195 Uiso 1 1 calc R U . . .
H19B H 0.809511 0.414018 0.054939 0.195 Uiso 1 1 calc R U . . .
C20 C 0.9433(8) 0.4291(10) 0.0529(4) 0.177(4) Uani 1 1 d D U . . .
H20A H 0.950584 0.361728 0.069190 0.213 Uiso 1 1 calc R U . . .
H20B H 0.947596 0.403629 0.026415 0.213 Uiso 1 1 calc R U . . .
C21 C 1.0983(7) 0.4485(7) 0.0605(2) 0.143(3) Uani 1 1 d D U . . .
H21A H 1.109106 0.414142 0.035500 0.171 Uiso 1 1 calc R U . . .
H21B H 1.097800 0.387150 0.079457 0.171 Uiso 1 1 calc R U . . .
C22 C 1.1715(6) 0.5267(8) 0.0693(3) 0.149(3) Uani 1 1 d D U . . .
H22A H 1.230461 0.487268 0.067332 0.179 Uiso 1 1 calc R U . . .
H22B H 1.171094 0.589521 0.050908 0.179 Uiso 1 1 calc R U . . .
C23 C 1.2345(5) 0.6462(7) 0.1165(3) 0.123(2) Uani 1 1 d D U . . .
H23A H 1.239331 0.706380 0.097302 0.148 Uiso 1 1 calc R U . . .
H23B H 1.292377 0.603945 0.117072 0.148 Uiso 1 1 calc R U . . .
C24 C 1.2174(5) 0.6980(8) 0.1547(2) 0.121(2) Uani 1 1 d D U . . .
H24A H 1.207064 0.637759 0.173502 0.145 Uiso 1 1 calc R U . . .
H24B H 1.270860 0.742404 0.162751 0.145 Uiso 1 1 calc R U . . .
C25 C 1.1192(5) 0.8250(6) 0.18818(18) 0.1017(19) Uani 1 1 d D U . . .
H25A H 1.169723 0.875825 0.195235 0.122 Uiso 1 1 calc R U . . .
H25B H 1.112868 0.767384 0.208201 0.122 Uiso 1 1 calc R U . . .
C26 C 1.0332(5) 0.8915(5) 0.18484(19) 0.0969(17) Uani 1 1 d D U . . .
H26A H 1.024697 0.938399 0.207634 0.116 Uiso 1 1 calc R U . . .
H26B H 1.035992 0.942015 0.162654 0.116 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
N1 C4 1.346(6) . ?
N1 H2 0.8600 . ?
N1 H1 0.8600 . ?
F1 C2 1.324(6) . ?
C1 C2 1.364(8) . ?
C1 C6 1.399(8) . ?
C1 C7 1.424(7) . ?
F2 C3 1.345(6) . ?
N2 C7 1.145(7) . ?
C2 C3 1.370(7) . ?
C3 C4 1.404(6) . ?
F3 C5 1.361(6) . ?
C4 C5 1.382(7) . ?
C5 C6 1.352(7) . ?
C6 H6 0.9300 . ?
N3 C11 1.318(6) . ?
N3 H4 0.8600 . ?
N3 H3 0.8600 . ?
N4 C14 1.128(7) . ?
F5 C10 1.356(5) . ?
F6 C12 1.345(5) . ?
C8 C9 1.380(7) . ?
C8 C13 1.387(7) . ?
C8 C14 1.442(7) . ?
C9 C10 1.365(6) . ?
C9 H13A 0.9300 . ?
C10 C11 1.398(6) . ?
C11 C12 1.416(6) . ?
C12 C13 1.340(6) . ?
C13 H13 0.9300 . ?
C13A F4A 1.233(13) . ?
O1 C26 1.424(7) . ?
O1 C15 1.433(7) . ?
O2 C16 1.404(6) . ?
O2 C17 1.408(7) . ?
O3 C18 1.237(9) . ?
O3 C19 1.354(9) . ?
O4 C20 1.355(10) . ?
O4 C21 1.367(11) . ?
O5 C22 1.407(9) . ?
O5 C23 1.413(9) . ?
O6 C24 1.412(8) . ?
O6 C25 1.427(7) . ?
C15 C16 1.457(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.412(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.408(12) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.427(11) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.478(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.467(9) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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
C4 N1 H2 120.0 . . ?
C4 N1 H1 120.0 . . ?
H2 N1 H1 120.0 . . ?
C2 C1 C6 117.1(4) . . ?
C2 C1 C7 121.1(5) . . ?
C6 C1 C7 121.8(5) . . ?
F1 C2 C1 119.8(4) . . ?
F1 C2 C3 118.0(5) . . ?
C1 C2 C3 122.2(4) . . ?
F2 C3 C2 120.4(4) . . ?
F2 C3 C4 117.6(4) . . ?
C2 C3 C4 122.0(5) . . ?
N1 C4 C5 125.1(4) . . ?
N1 C4 C3 121.0(5) . . ?
C5 C4 C3 113.9(4) . . ?
C6 C5 F3 118.4(5) . . ?
C6 C5 C4 125.1(5) . . ?
F3 C5 C4 116.5(4) . . ?
C5 C6 C1 119.7(5) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 C7 C1 178.1(7) . . ?
C11 N3 H4 120.0 . . ?
C11 N3 H3 120.0 . . ?
H4 N3 H3 120.0 . . ?
C9 C8 C13 118.0(4) . . ?
C9 C8 C14 120.0(4) . . ?
C13 C8 C14 121.9(4) . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H13A 119.6 . . ?
C8 C9 H13A 119.6 . . ?
F5 C10 C9 119.7(4) . . ?
F5 C10 C11 117.1(4) . . ?
C9 C10 C11 123.1(4) . . ?
N3 C11 C10 123.1(4) . . ?
N3 C11 C12 123.3(4) . . ?
C10 C11 C12 113.6(4) . . ?
C13 C12 F6 120.6(4) . . ?
C13 C12 C11 124.0(4) . . ?
F6 C12 C11 115.3(4) . . ?
C12 C13 C8 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
N4 C14 C8 175.8(7) . . ?
C26 O1 C15 111.3(4) . . ?
C16 O2 C17 113.6(4) . . ?
C18 O3 C19 124.0(9) . . ?
C20 O4 C21 112.7(8) . . ?
C22 O5 C23 111.4(6) . . ?
C24 O6 C25 112.4(5) . . ?
O1 C15 C16 109.3(5) . . ?
O1 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
O1 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
O2 C16 C15 110.6(4) . . ?
O2 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
O2 C17 C18 114.1(5) . . ?
O2 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
O2 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
O3 C18 C17 123.2(8) . . ?
O3 C18 H18A 106.5 . . ?
C17 C18 H18A 106.5 . . ?
O3 C18 H18B 106.5 . . ?
C17 C18 H18B 106.5 . . ?
H18A C18 H18B 106.5 . . ?
O3 C19 C20 116.1(10) . . ?
O3 C19 H19A 108.3 . . ?
C20 C19 H19A 108.3 . . ?
O3 C19 H19B 108.3 . . ?
C20 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
O4 C20 C19 115.2(8) . . ?
O4 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
O4 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
O4 C21 C22 111.7(7) . . ?
O4 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
O4 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
O5 C22 C21 110.4(6) . . ?
O5 C22 H22A 109.6 . . ?
C21 C22 H22A 109.6 . . ?
O5 C22 H22B 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
O5 C23 C24 109.8(6) . . ?
O5 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
O5 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
O6 C24 C23 109.3(6) . . ?
O6 C24 H24A 109.8 . . ?
C23 C24 H24A 109.8 . . ?
O6 C24 H24B 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.3 . . ?
O6 C25 C26 109.9(5) . . ?
O6 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
O6 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
O1 C26 C25 108.4(5) . . ?
O1 C26 H26A 110.0 . . ?
C25 C26 H26A 110.0 . . ?
O1 C26 H26B 110.0 . . ?
C25 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?

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
C6 C1 C2 F1 -179.8(4) . . . . ?
C7 C1 C2 F1 0.5(7) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
C7 C1 C2 C3 -178.9(5) . . . . ?
F1 C2 C3 F2 1.1(7) . . . . ?
C1 C2 C3 F2 -179.5(4) . . . . ?
F1 C2 C3 C4 -179.4(4) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
F2 C3 C4 N1 -0.7(6) . . . . ?
C2 C3 C4 N1 179.8(4) . . . . ?
F2 C3 C4 C5 178.5(4) . . . . ?
C2 C3 C4 C5 -0.9(6) . . . . ?
N1 C4 C5 C6 -179.7(5) . . . . ?
C3 C4 C5 C6 1.1(7) . . . . ?
N1 C4 C5 F3 0.1(7) . . . . ?
C3 C4 C5 F3 -179.1(4) . . . . ?
F3 C5 C6 C1 180.0(4) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C2 C1 C6 C5 -0.7(7) . . . . ?
C7 C1 C6 C5 179.0(5) . . . . ?
C13 C8 C9 C10 -1.4(7) . . . . ?
C14 C8 C9 C10 177.6(5) . . . . ?
C8 C9 C10 F5 -177.3(4) . . . . ?
C8 C9 C10 C11 1.2(7) . . . . ?
F5 C10 C11 N3 -3.1(7) . . . . ?
C9 C10 C11 N3 178.4(5) . . . . ?
F5 C10 C11 C12 178.4(4) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
N3 C11 C12 C13 -179.2(5) . . . . ?
C10 C11 C12 C13 -0.8(7) . . . . ?
N3 C11 C12 F6 3.2(7) . . . . ?
C10 C11 C12 F6 -178.3(4) . . . . ?
F6 C12 C13 C8 177.9(4) . . . . ?
C11 C12 C13 C8 0.5(7) . . . . ?
C9 C8 C13 C12 0.6(7) . . . . ?
C14 C8 C13 C12 -178.3(5) . . . . ?
C26 O1 C15 C16 -178.5(5) . . . . ?
C17 O2 C16 C15 173.0(6) . . . . ?
O1 C15 C16 O2 -62.9(7) . . . . ?
C16 O2 C17 C18 -179.1(7) . . . . ?
C19 O3 C18 C17 -163.1(10) . . . . ?
O2 C17 C18 O3 35.3(15) . . . . ?
C18 O3 C19 C20 -166.6(12) . . . . ?
C21 O4 C20 C19 169.5(10) . . . . ?
O3 C19 C20 O4 -53.2(17) . . . . ?
C20 O4 C21 C22 -178.4(9) . . . . ?
C23 O5 C22 C21 178.3(8) . . . . ?
O4 C21 C22 O5 63.6(11) . . . . ?
C22 O5 C23 C24 175.4(7) . . . . ?
C25 O6 C24 C23 -178.9(6) . . . . ?
O5 C23 C24 O6 -66.2(9) . . . . ?
C24 O6 C25 C26 -175.6(6) . . . . ?
C15 O1 C26 C25 -174.7(5) . . . . ?
O6 C25 C26 O1 68.7(7) . . . . ?

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.067


####################################################################### 
# 
# 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_C-M96
_database_code_depnum_ccdc_archive 'CCDC 2118105'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        4-amino-2,3,5-trifluorobenzonitrile
_chemical_name_common            ?
_chemical_melting_point          369
_chemical_formula_moiety         'C7 H3 F3 N2'
_chemical_formula_sum            'C7 H3 F3 N2'
_chemical_formula_weight         172.11

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   3.7360(7)
_cell_length_b                   8.4997(17)
_cell_length_c                   10.654(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.061(7)
_cell_angle_gamma                90
_cell_volume                     336.44(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1346
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      25.73

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_F_000             172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8193
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2291
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         25.828
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.863
_reflns_number_total             1092
_reflns_number_gt                990
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_max     0.674
_reflns_Friedel_fraction_full    0.713

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0977P)²+0.0066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1092
_refine_ls_number_parameters     117
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   0.815
_refine_ls_restrained_S_all      0.813
_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 0.3925(5) 0.7631(2) 0.08363(17) 0.0417(5) Uani 1 1 d . . . . .
N1 N 0.2035(9) 1.2956(3) 0.1873(3) 0.0415(7) Uani 1 1 d D . . . .
H2 H 0.218(11) 1.367(4) 0.248(3) 0.049(11) Uiso 1 1 d D . . . .
H1 H 0.064(10) 1.309(5) 0.115(3) 0.050(10) Uiso 1 1 d D . . . .
C1 C 0.6246(7) 0.8507(3) 0.2867(3) 0.0270(6) Uani 1 1 d . . . . .
F2 F 0.1187(4) 1.0452(3) 0.02198(14) 0.0412(5) Uani 1 1 d . . . . .
C2 C 0.4398(8) 0.8796(3) 0.1691(3) 0.0281(7) Uani 1 1 d . . . . .
N2 N 0.8991(7) 0.5768(4) 0.3355(2) 0.0430(7) Uani 1 1 d . . . . .
F3 F 0.5587(6) 1.2408(2) 0.42038(18) 0.0460(6) Uani 1 1 d . . . . .
C3 C 0.3018(7) 1.0255(4) 0.1365(2) 0.0283(7) Uani 1 1 d . . . . .
C4 C 0.3348(8) 1.1523(3) 0.2194(3) 0.0292(7) Uani 1 1 d . . . . .
C5 C 0.5219(8) 1.1188(4) 0.3380(3) 0.0309(7) Uani 1 1 d . . . . .
C6 C 0.6632(8) 0.9760(3) 0.3725(3) 0.0293(7) Uani 1 1 d . . . . .
H6 H 0.787206 0.961216 0.454218 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7733(8) 0.6984(4) 0.3150(3) 0.0316(7) Uani 1 1 d . . . . .


_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 C2 1.344(3) . ?
N1 C4 1.344(4) . ?
N1 H2 0.89(2) . ?
N1 H1 0.89(2) . ?
C1 C2 1.387(4) . ?
C1 C6 1.401(4) . ?
C1 C7 1.429(4) . ?
F2 C3 1.345(3) . ?
C2 C3 1.373(4) . ?
N2 C7 1.147(4) . ?
F3 C5 1.356(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.407(4) . ?
C5 C6 1.359(4) . ?
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
C4 N1 H2 116(3) . . ?
C4 N1 H1 120(3) . . ?
H2 N1 H1 122(4) . . ?
C2 C1 C6 117.5(3) . . ?
C2 C1 C7 119.8(3) . . ?
C6 C1 C7 122.7(3) . . ?
F1 C2 C3 118.4(2) . . ?
F1 C2 C1 119.9(3) . . ?
C3 C2 C1 121.7(3) . . ?
F2 C3 C2 118.9(3) . . ?
F2 C3 C4 118.8(3) . . ?
C2 C3 C4 122.2(2) . . ?
N1 C4 C3 122.4(3) . . ?
N1 C4 C5 123.0(3) . . ?
C3 C4 C5 114.6(3) . . ?
F3 C5 C6 119.9(2) . . ?
F3 C5 C4 115.7(3) . . ?
C6 C5 C4 124.4(3) . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N2 C7 C1 178.2(4) . . ?

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
C6 C1 C2 F1 -179.4(2) . . . . ?
C7 C1 C2 F1 1.9(4) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C7 C1 C2 C3 -178.0(3) . . . . ?
F1 C2 C3 F2 1.4(4) . . . . ?
C1 C2 C3 F2 -178.6(2) . . . . ?
F1 C2 C3 C4 179.3(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
F2 C3 C4 N1 -2.9(4) . . . . ?
C2 C3 C4 N1 179.2(3) . . . . ?
F2 C3 C4 C5 178.3(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
N1 C4 C5 F3 1.0(4) . . . . ?
C3 C4 C5 F3 179.8(3) . . . . ?
N1 C4 C5 C6 -178.8(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
F3 C5 C6 C1 -179.8(2) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C7 C1 C6 C5 178.4(3) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041


####################################################################### 
# 
# 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_2Ecr-M26
_database_code_depnum_ccdc_archive 'CCDC 2118103'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2-amino-4-chloro-3,6-difluorobenzonitrile 18-crown-6 associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          390
_chemical_formula_moiety         '2(C7 H3 Cl F2 N2), C12 H24 O6'
_chemical_formula_sum            'C26 H30 Cl2 F4 N4 O6'
_chemical_formula_weight         641.44

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   9.2760(4)
_cell_length_b                   9.8840(5)
_cell_length_c                   10.2679(5)
_cell_angle_alpha                111.106(2)
_cell_angle_beta                 98.506(2)
_cell_angle_gamma                116.108(2)
_cell_volume                     734.00(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.293
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7724
_exptl_absorpt_correction_T_max  0.8372
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20065
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         28.043
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3547
_reflns_number_gt                3009
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0555P)²+0.2075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3547
_refine_ls_number_parameters     198
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.036
_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
Cl1 Cl 1.33654(5) 0.60055(5) 0.42854(5) 0.05965(15) Uani 1 1 d . . . . .
N2 N 0.6208(2) -0.0920(2) 0.4135(2) 0.0770(5) Uani 1 1 d . . . . .
C1 C 0.87780(17) 0.15968(17) 0.41556(15) 0.0400(3) Uani 1 1 d . . . . .
F1 F 0.98429(12) 0.40978(11) 0.22124(10) 0.0542(2) Uani 1 1 d . . . . .
N1 N 0.69962(15) 0.14211(16) 0.20337(14) 0.0425(3) Uani 1 1 d D . . . .
H1 H 0.623(2) 0.0389(19) 0.183(2) 0.054(5) Uiso 1 1 d D . . . .
H2 H 0.701(2) 0.158(2) 0.1261(18) 0.053(5) Uiso 1 1 d D . . . .
C2 C 0.85499(16) 0.21379(15) 0.30886(14) 0.0341(3) Uani 1 1 d . . . . .
F2 F 1.05591(15) 0.18896(17) 0.62423(13) 0.0795(4) Uani 1 1 d . . . . .
C3 C 1.00314(17) 0.35424(16) 0.32120(14) 0.0368(3) Uani 1 1 d . . . . .
C4 C 1.16244(18) 0.43288(17) 0.42691(16) 0.0422(3) Uani 1 1 d . . . . .
C5 C 1.18489(19) 0.3775(2) 0.53079(17) 0.0525(4) Uani 1 1 d . . . . .
H5 H 1.292802 0.429259 0.602381 0.063 Uiso 1 1 calc R U . . .
C6 C 1.0412(2) 0.2436(2) 0.52309(17) 0.0499(4) Uani 1 1 d . . . . .
C7 C 0.7345(2) 0.0193(2) 0.41426(17) 0.0505(4) Uani 1 1 d . . . . .
O1 O 0.21918(15) 1.00687(14) 0.08684(12) 0.0499(3) Uani 1 1 d . . . . .
O2 O 0.34646(12) 0.79803(12) 0.07440(12) 0.0435(2) Uani 1 1 d . . . . .
O3 O 0.63372(15) 0.77301(15) 0.04699(14) 0.0571(3) Uani 1 1 d . . . . .
C8 C 0.2383(3) 1.1691(3) 0.1350(3) 0.0723(6) Uani 1 1 d . . . . .
H8A H 0.347027 1.256006 0.218393 0.087 Uiso 1 1 calc R U . . .
H8B H 0.146061 1.167686 0.169576 0.087 Uiso 1 1 calc R U . . .
C9 C 0.2556(2) 0.9765(2) 0.20895(18) 0.0539(4) Uani 1 1 d . . . . .
H9A H 0.179264 0.982719 0.262821 0.065 Uiso 1 1 calc R U . . .
H9B H 0.373567 1.063012 0.277807 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2303(2) 0.8030(2) 0.15001(19) 0.0521(4) Uani 1 1 d . . . . .
H10A H 0.252081 0.779096 0.232041 0.063 Uiso 1 1 calc R U . . .
H10B H 0.112340 0.716448 0.081137 0.063 Uiso 1 1 calc R U . . .
C11 C 0.3428(2) 0.64199(19) 0.0279(2) 0.0544(4) Uani 1 1 d . . . . .
H11A H 0.226770 0.545070 -0.037036 0.065 Uiso 1 1 calc R U . . .
H11B H 0.377994 0.629644 0.114621 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4648(2) 0.6468(2) -0.05506(19) 0.0571(4) Uani 1 1 d . . . . .
H12A H 0.452709 0.535890 -0.100275 0.068 Uiso 1 1 calc R U . . .
H12B H 0.438142 0.673356 -0.134209 0.068 Uiso 1 1 calc R U . . .
C13 C 0.7661(3) 0.7867(3) -0.0111(3) 0.0734(6) Uani 1 1 d . . . . .
H13A H 0.759721 0.678299 -0.046846 0.088 Uiso 1 1 calc R U . . .
H13B H 0.876533 0.873434 0.070299 0.088 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
Cl1 C4 1.7237(14) . ?
N2 C7 1.137(2) . ?
C1 C6 1.394(2) . ?
C1 C2 1.4086(18) . ?
C1 C7 1.4318(19) . ?
F1 C3 1.3500(15) . ?
N1 C2 1.3562(18) . ?
C2 C3 1.4051(17) . ?
F2 C6 1.3475(17) . ?
C3 C4 1.369(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.369(2) . ?
O1 C8 1.414(2) . ?
O1 C9 1.4184(19) . ?
O2 C11 1.4235(18) . ?
O2 C10 1.4256(18) . ?
O3 C12 1.401(2) . ?
O3 C13 1.418(2) . ?
C8 C13 1.486(3) 2_675 ?
C9 C10 1.489(2) . ?
C11 C12 1.509(3) . ?

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 C1 C2 119.64(12) . . ?
C6 C1 C7 119.88(13) . . ?
C2 C1 C7 120.48(12) . . ?
N1 C2 C3 120.65(12) . . ?
N1 C2 C1 123.25(12) . . ?
C3 C2 C1 116.04(12) . . ?
F1 C3 C4 119.78(12) . . ?
F1 C3 C2 117.18(12) . . ?
C4 C3 C2 123.02(12) . . ?
C3 C4 C5 120.75(13) . . ?
C3 C4 Cl1 119.10(11) . . ?
C5 C4 Cl1 120.14(11) . . ?
C6 C5 C4 117.12(13) . . ?
F2 C6 C5 119.19(14) . . ?
F2 C6 C1 117.42(13) . . ?
C5 C6 C1 123.39(14) . . ?
N2 C7 C1 179.87(15) . . ?
C8 O1 C9 111.82(14) . . ?
C11 O2 C10 112.36(12) . . ?
C12 O3 C13 115.83(15) . . ?
O1 C8 C13 110.96(16) . 2_675 ?
O1 C9 C10 108.88(13) . . ?
O2 C10 C9 108.93(12) . . ?
O2 C11 C12 108.26(12) . . ?
O3 C12 C11 108.56(14) . . ?
O3 C13 C8 115.81(17) . 2_675 ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_2Dcr-M25
_database_code_depnum_ccdc_archive 'CCDC 2118102'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2-amino-4-chloro-3,5,6-trifluorobenzonitrile 18-crown-6 associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          371
_chemical_formula_moiety         '2(C7 H2 Cl F3 N1), C12 H24 O6'
_chemical_formula_sum            'C26 H28 Cl2 F6 N4 O6'
_chemical_formula_weight         677.42

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   9.4276(6)
_cell_length_b                   9.9092(6)
_cell_length_c                   10.3213(7)
_cell_angle_alpha                111.749(2)
_cell_angle_beta                 97.219(3)
_cell_angle_gamma                116.798(2)
_cell_volume                     747.91(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.88

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    0.301
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8058
_exptl_absorpt_correction_T_max  0.8372
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20110
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         27.910
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3585
_reflns_number_gt                3092
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0434P)²+0.2376P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3585
_refine_ls_number_parameters     207
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.032
_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
Cl1 Cl 1.32845(5) 1.10514(5) 0.91563(5) 0.05709(13) Uani 1 1 d . . . . .
F1 F 0.97746(12) 0.91796(11) 0.71854(10) 0.0546(2) Uani 1 1 d . . . . .
N2 N 0.6214(2) 0.4197(2) 0.91805(19) 0.0726(5) Uani 1 1 d . . . . .
C1 C 0.87468(17) 0.66494(17) 0.90902(15) 0.0393(3) Uani 1 1 d . . . . .
N1 N 0.69626(15) 0.65159(16) 0.70624(14) 0.0438(3) Uani 1 1 d D . . . .
H1 H 0.696(2) 0.662(2) 0.6277(18) 0.061(5) Uiso 1 1 d D . . . .
H2 H 0.618(2) 0.5465(19) 0.684(2) 0.058(5) Uiso 1 1 d D . . . .
C2 C 0.85112(16) 0.72031(16) 0.80531(14) 0.0348(3) Uani 1 1 d . . . . .
F2 F 1.33036(12) 0.94773(15) 1.10767(12) 0.0738(3) Uani 1 1 d . . . . .
C3 C 0.99694(17) 0.85961(16) 0.81441(14) 0.0368(3) Uani 1 1 d . . . . .
F3 F 1.05473(14) 0.69072(15) 1.10944(12) 0.0736(3) Uani 1 1 d . . . . .
C4 C 1.15590(17) 0.93736(17) 0.91361(15) 0.0402(3) Uani 1 1 d . . . . .
C5 C 1.17574(18) 0.87752(19) 1.01202(16) 0.0466(3) Uani 1 1 d . . . . .
C6 C 1.0361(2) 0.7448(2) 1.01056(16) 0.0467(3) Uani 1 1 d . . . . .
C7 C 0.7329(2) 0.5272(2) 0.91278(16) 0.0488(3) Uani 1 1 d . . . . .
O1 O 0.21661(14) 0.50658(14) 0.58331(12) 0.0507(3) Uani 1 1 d . . . . .
O2 O 0.35095(12) 0.30662(12) 0.57997(11) 0.0445(2) Uani 1 1 d . . . . .
O3 O 0.63829(15) 0.28477(15) 0.56010(13) 0.0558(3) Uani 1 1 d . . . . .
C8 C 0.2349(3) 0.6686(2) 0.6263(2) 0.0687(5) Uani 1 1 d . . . . .
H8A H 0.341812 0.758737 0.707880 0.082 Uiso 1 1 calc R U . . .
H8B H 0.143751 0.668561 0.660699 0.082 Uiso 1 1 calc R U . . .
C9 C 0.2550(2) 0.4829(2) 0.70733(18) 0.0552(4) Uani 1 1 d . . . . .
H9A H 0.179546 0.489670 0.761734 0.066 Uiso 1 1 calc R U . . .
H9B H 0.370828 0.573175 0.774093 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2340(2) 0.3111(2) 0.65400(19) 0.0534(4) Uani 1 1 d . . . . .
H10A H 0.255475 0.291677 0.737822 0.064 Uiso 1 1 calc R U . . .
H10B H 0.118737 0.220849 0.585928 0.064 Uiso 1 1 calc R U . . .
C11 C 0.3492(2) 0.15180(19) 0.53748(19) 0.0519(4) Uani 1 1 d . . . . .
H11A H 0.235832 0.052642 0.472900 0.062 Uiso 1 1 calc R U . . .
H11B H 0.382041 0.142456 0.625162 0.062 Uiso 1 1 calc R U . . .
C12 C 0.4716(2) 0.1561(2) 0.45713(18) 0.0544(4) Uani 1 1 d . . . . .
H12A H 0.459481 0.044609 0.413204 0.065 Uiso 1 1 calc R U . . .
H12B H 0.448300 0.181579 0.377786 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7696(3) 0.2955(3) 0.5024(3) 0.0700(5) Uani 1 1 d . . . . .
H13A H 0.763928 0.187470 0.471273 0.084 Uiso 1 1 calc R U . . .
H13B H 0.877945 0.385767 0.582218 0.084 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
Cl1 C4 1.7141(14) . ?
F1 C3 1.3496(15) . ?
N2 C7 1.136(2) . ?
C1 C6 1.393(2) . ?
C1 C2 1.4077(18) . ?
C1 C7 1.4346(19) . ?
N1 C2 1.3612(18) . ?
C2 C3 1.4016(18) . ?
F2 C5 1.3411(17) . ?
C3 C4 1.3698(19) . ?
F3 C6 1.3431(17) . ?
C4 C5 1.384(2) . ?
C5 C6 1.372(2) . ?
O1 C8 1.417(2) . ?
O1 C9 1.4165(19) . ?
O2 C11 1.4224(18) . ?
O2 C10 1.4252(18) . ?
O3 C12 1.412(2) . ?
O3 C13 1.418(2) . ?
C8 C13 1.498(3) 2_666 ?
C9 C10 1.489(2) . ?
C11 C12 1.498(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
C6 C1 C2 120.28(12) . . ?
C6 C1 C7 119.14(13) . . ?
C2 C1 C7 120.57(12) . . ?
N1 C2 C3 120.63(12) . . ?
N1 C2 C1 123.26(12) . . ?
C3 C2 C1 116.02(12) . . ?
F1 C3 C4 119.02(12) . . ?
F1 C3 C2 117.30(12) . . ?
C4 C3 C2 123.68(12) . . ?
C3 C4 C5 118.98(12) . . ?
C3 C4 Cl1 120.79(11) . . ?
C5 C4 Cl1 120.24(11) . . ?
F2 C5 C6 120.01(14) . . ?
F2 C5 C4 120.40(13) . . ?
C6 C5 C4 119.59(13) . . ?
F3 C6 C5 119.53(13) . . ?
F3 C6 C1 119.05(13) . . ?
C5 C6 C1 121.41(13) . . ?
N2 C7 C1 178.95(18) . . ?
C8 O1 C9 112.27(13) . . ?
C11 O2 C10 112.16(11) . . ?
C12 O3 C13 115.20(14) . . ?
O1 C8 C13 110.44(15) . 2_666 ?
O1 C9 C10 109.28(13) . . ?
O2 C10 C9 108.89(12) . . ?
O2 C11 C12 108.48(12) . . ?
O3 C12 C11 108.68(13) . . ?
O3 C13 C8 115.49(16) . 2_666 ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.036



