# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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-c1042
_database_code_depnum_ccdc_archive 'CCDC 1911494'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-amino-3-chloro-2,5,6-trifluoropyridine
_chemical_name_common            ?
_chemical_melting_point          392
_chemical_formula_moiety         'C5 H2 Cl F3 N2'
_chemical_formula_sum            'C5 H2 Cl F3 N2'
_chemical_formula_weight         182.54

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'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   9.2213(16)
_cell_length_b                   13.783(2)
_cell_length_c                   5.0802(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     645.70(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2017
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      24.95

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.576
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6421
_exptl_absorpt_correction_T_max  0.7453
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4219
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.658
_diffrn_reflns_theta_max         26.112
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.925
_reflns_number_total             1127
_reflns_number_gt                954
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.810
_reflns_Friedel_fraction_full    0.865

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1108P)²+0.4019P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1127
_refine_ls_number_parameters     106
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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 -0.0092(2) 0.39070(11) 0.1904(6) 0.0436(6) Uani 1 1 d . . . . .
N1 N 0.2272(6) 0.2297(4) 0.6783(14) 0.0359(14) Uani 1 1 d . . . . .
F1 F 0.2085(5) 0.3903(3) 0.6184(9) 0.0481(13) Uani 1 1 d . . . . .
C1 C 0.1650(7) 0.3012(4) 0.5433(16) 0.0334(17) Uani 1 1 d . . . . .
N2 N -0.0752(6) 0.1788(4) 0.0811(11) 0.0294(13) Uani 1 1 d . . . . .
H2A H -0.126(8) 0.225(5) -0.004(16) 0.034 Uiso 1 1 d . U . . .
H2B H -0.100(8) 0.122(6) 0.052(17) 0.034 Uiso 1 1 d . U . . .
F2 F 0.0597(5) 0.0286(3) 0.3430(9) 0.0445(12) Uani 1 1 d . . . . .
C2 C 0.0642(7) 0.2920(5) 0.3502(15) 0.0268(14) Uani 1 1 d . . . . .
F3 F 0.2491(5) 0.0677(3) 0.7359(9) 0.0533(14) Uani 1 1 d . . . . .
C3 C 0.0228(7) 0.1970(4) 0.2701(12) 0.0226(15) Uani 1 1 d . . . . .
C4 C 0.0913(7) 0.1210(4) 0.4082(15) 0.0290(15) Uani 1 1 d . . . . .
C5 C 0.1872(7) 0.1412(5) 0.6050(13) 0.0300(15) 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 C2 1.723(7) . ?
N1 C5 1.328(9) . ?
N1 C1 1.331(9) . ?
F1 C1 1.347(7) . ?
C1 C2 1.358(11) . ?
N2 C3 1.342(9) . ?
F2 C4 1.348(7) . ?
C2 C3 1.423(8) . ?
F3 C5 1.339(7) . ?
C3 C4 1.409(9) . ?
C4 C5 1.363(10) . ?

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
C5 N1 C1 114.6(6) . . ?
N1 C1 C2 126.7(6) . . ?
N1 C1 F1 113.6(7) . . ?
C2 C1 F1 119.6(6) . . ?
C1 C2 C3 118.5(6) . . ?
C1 C2 Cl1 122.4(5) . . ?
C3 C2 Cl1 119.1(5) . . ?
N2 C3 C2 123.8(6) . . ?
N2 C3 C4 121.3(6) . . ?
C2 C3 C4 114.9(6) . . ?
F2 C4 C5 120.8(6) . . ?
F2 C4 C3 118.8(6) . . ?
C5 C4 C3 120.3(6) . . ?
F3 C5 N1 115.9(6) . . ?
F3 C5 C4 119.1(6) . . ?
N1 C5 C4 124.9(6) . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.303
_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-m_998
_database_code_depnum_ccdc_archive 'CCDC 1911495'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-amino-3,5-dichloro-2,6-difluoropyridine
_chemical_name_common            ?
_chemical_melting_point          387
_chemical_formula_moiety         'C5 H2 Cl2 F2 N2'
_chemical_formula_sum            'C5 H2 Cl2 F2 N2'
_chemical_formula_weight         198.99

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                   15.0718(7)
_cell_length_b                   13.6626(5)
_cell_length_c                   7.0649(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.519(2)
_cell_angle_gamma                90
_cell_volume                     1453.40(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.08

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.857
_shelx_estimated_absorpt_T_min   0.627
_shelx_estimated_absorpt_T_max   0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5101
_exptl_absorpt_correction_T_max  0.5632
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27163
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.352
_diffrn_reflns_theta_max         28.004
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3498
_reflns_number_gt                2758
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0660P)²+0.9981P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0074(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3498
_refine_ls_number_parameters     216
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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 0.71584(5) 0.13076(6) 0.05928(12) 0.0789(3) Uani 1 1 d . . . . .
F1 F 0.72046(11) 0.12423(13) 0.4754(3) 0.0748(5) Uani 1 1 d . . . . .
N1 N 0.57399(14) 0.12184(15) 0.5163(3) 0.0531(5) Uani 1 1 d . . . . .
C1 C 0.63809(16) 0.12444(17) 0.3967(3) 0.0493(5) Uani 1 1 d . . . . .
Cl2 Cl 0.36240(5) 0.12339(8) 0.16825(13) 0.0867(3) Uani 1 1 d . . . . .
F2 F 0.42841(12) 0.11983(16) 0.5625(2) 0.0819(6) Uani 1 1 d . . . . .
N2 N 0.5235(2) 0.1277(2) -0.0654(3) 0.0699(7) Uani 1 1 d D . . . .
H2B H 0.5649(14) 0.133(2) -0.141(4) 0.080(11) Uiso 1 1 d D . . . .
H2A H 0.4711(8) 0.130(2) -0.111(4) 0.062(9) Uiso 1 1 d D . . . .
C2 C 0.62709(15) 0.12673(16) 0.2040(3) 0.0465(5) Uani 1 1 d . . . . .
C3 C 0.54023(16) 0.12600(16) 0.1227(3) 0.0456(5) Uani 1 1 d . . . . .
C4 C 0.47119(15) 0.12362(17) 0.2493(3) 0.0486(5) Uani 1 1 d . . . . .
C5 C 0.49365(16) 0.12217(18) 0.4389(3) 0.0503(5) Uani 1 1 d . . . . .
Cl3 Cl 0.23023(4) 0.39414(6) 0.16007(14) 0.0766(3) Uani 1 1 d . . . . .
F3 F 0.16281(11) 0.19661(12) 0.2004(3) 0.0872(6) Uani 1 1 d . . . . .
N3 N 0.02108(14) 0.23048(15) 0.2597(3) 0.0595(5) Uani 1 1 d . . . . .
N4 N 0.07383(15) 0.52841(15) 0.2072(3) 0.0546(5) Uani 1 1 d D . . . .
H4B H 0.0354(14) 0.5733(15) 0.217(4) 0.068(9) Uiso 1 1 d D . . . .
H4A H 0.1255(9) 0.549(2) 0.193(4) 0.067(9) Uiso 1 1 d D . . . .
Cl4 Cl -0.11436(4) 0.47757(5) 0.28904(10) 0.0628(2) Uani 1 1 d . . . . .
F4 F -0.11992(10) 0.26340(13) 0.3191(3) 0.0782(5) Uani 1 1 d . . . . .
C6 C 0.10052(16) 0.26456(19) 0.2241(4) 0.0565(6) Uani 1 1 d . . . . .
C7 C 0.12311(15) 0.36106(18) 0.2063(4) 0.0498(5) Uani 1 1 d . . . . .
C8 C 0.05699(14) 0.43249(16) 0.2258(3) 0.0428(5) Uani 1 1 d . . . . .
C9 C -0.02821(15) 0.39707(16) 0.2641(3) 0.0447(5) Uani 1 1 d . . . . .
C10 C -0.03986(16) 0.29783(19) 0.2801(4) 0.0531(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
Cl1 C2 1.720(2) . ?
F1 C1 1.338(3) . ?
N1 C5 1.307(3) . ?
N1 C1 1.311(3) . ?
C1 C2 1.364(3) . ?
Cl2 C4 1.713(2) . ?
F2 C5 1.344(3) . ?
N2 C3 1.342(3) . ?
N2 H2B 0.840(10) . ?
N2 H2A 0.840(10) . ?
C2 C3 1.407(3) . ?
C3 C4 1.402(3) . ?
C4 C5 1.368(3) . ?
Cl3 C7 1.721(2) . ?
F3 C6 1.336(3) . ?
N3 C10 1.312(3) . ?
N3 C6 1.319(3) . ?
N4 C8 1.342(3) . ?
N4 H4B 0.848(10) . ?
N4 H4A 0.841(10) . ?
Cl4 C9 1.717(2) . ?
F4 C10 1.335(3) . ?
C6 C7 1.369(3) . ?
C7 C8 1.406(3) . ?
C8 C9 1.410(3) . ?
C9 C10 1.373(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
C5 N1 C1 115.2(2) . . ?
N1 C1 F1 115.4(2) . . ?
N1 C1 C2 125.6(2) . . ?
F1 C1 C2 119.0(2) . . ?
C3 N2 H2B 121(2) . . ?
C3 N2 H2A 121(2) . . ?
H2B N2 H2A 118(3) . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 Cl1 122.03(19) . . ?
C3 C2 Cl1 119.44(18) . . ?
N2 C3 C4 121.3(2) . . ?
N2 C3 C2 122.4(2) . . ?
C4 C3 C2 116.32(19) . . ?
C5 C4 C3 117.8(2) . . ?
C5 C4 Cl2 121.30(19) . . ?
C3 C4 Cl2 120.89(17) . . ?
N1 C5 F2 114.8(2) . . ?
N1 C5 C4 126.5(2) . . ?
F2 C5 C4 118.7(2) . . ?
C10 N3 C6 114.8(2) . . ?
C8 N4 H4B 124.5(19) . . ?
C8 N4 H4A 122(2) . . ?
H4B N4 H4A 114(2) . . ?
N3 C6 F3 115.3(2) . . ?
N3 C6 C7 126.1(2) . . ?
F3 C6 C7 118.6(2) . . ?
C6 C7 C8 118.6(2) . . ?
C6 C7 Cl3 120.63(19) . . ?
C8 C7 Cl3 120.73(18) . . ?
N4 C8 C7 122.0(2) . . ?
N4 C8 C9 122.1(2) . . ?
C7 C8 C9 115.9(2) . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 Cl4 121.63(18) . . ?
C8 C9 Cl4 119.95(17) . . ?
N3 C10 F4 114.8(2) . . ?
N3 C10 C9 126.2(2) . . ?
F4 C10 C9 119.0(2) . . ?

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
C5 N1 C1 F1 179.9(2) . . . . ?
C5 N1 C1 C2 -0.4(4) . . . . ?
N1 C1 C2 C3 -0.2(4) . . . . ?
F1 C1 C2 C3 179.4(2) . . . . ?
N1 C1 C2 Cl1 179.6(2) . . . . ?
F1 C1 C2 Cl1 -0.8(3) . . . . ?
C1 C2 C3 N2 -179.7(2) . . . . ?
Cl1 C2 C3 N2 0.5(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
Cl1 C2 C3 C4 -179.40(18) . . . . ?
N2 C3 C4 C5 -179.9(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
N2 C3 C4 Cl2 -0.3(3) . . . . ?
C2 C3 C4 Cl2 179.53(17) . . . . ?
C1 N1 C5 F2 -179.8(2) . . . . ?
C1 N1 C5 C4 0.9(4) . . . . ?
C3 C4 C5 N1 -0.7(4) . . . . ?
Cl2 C4 C5 N1 179.7(2) . . . . ?
C3 C4 C5 F2 -180.0(2) . . . . ?
Cl2 C4 C5 F2 0.5(3) . . . . ?
C10 N3 C6 F3 -179.1(2) . . . . ?
C10 N3 C6 C7 -0.4(4) . . . . ?
N3 C6 C7 C8 -0.4(4) . . . . ?
F3 C6 C7 C8 178.2(2) . . . . ?
N3 C6 C7 Cl3 179.8(2) . . . . ?
F3 C6 C7 Cl3 -1.6(4) . . . . ?
C6 C7 C8 N4 -178.9(2) . . . . ?
Cl3 C7 C8 N4 0.8(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
Cl3 C7 C8 C9 -179.78(17) . . . . ?
N4 C8 C9 C10 179.7(2) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
N4 C8 C9 Cl4 -0.1(3) . . . . ?
C7 C8 C9 Cl4 -179.51(17) . . . . ?
C6 N3 C10 F4 -179.0(2) . . . . ?
C6 N3 C10 C9 1.3(4) . . . . ?
C8 C9 C10 N3 -1.3(4) . . . . ?
Cl4 C9 C10 N3 178.5(2) . . . . ?
C8 C9 C10 F4 179.0(2) . . . . ?
Cl4 C9 C10 F4 -1.1(3) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.052

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_D-mc743
_database_code_depnum_ccdc_archive 'CCDC 1911496'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-amino-3,5,6-trifluoropyridine
_chemical_name_common            ?
_chemical_melting_point          372
_chemical_formula_moiety         'C5 H3 F3 N2'
_chemical_formula_sum            'C5 H3 F3 N2'
_chemical_formula_weight         148.09

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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   3.6538(3)
_cell_length_b                   7.6296(8)
_cell_length_c                   20.158(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.323(4)
_cell_angle_gamma                90
_cell_volume                     561.79(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5691
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      30.44

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8812
_exptl_absorpt_correction_T_max  0.9391
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16065
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.855
_diffrn_reflns_theta_max         30.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1711
_reflns_number_gt                1386
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0344P)²+0.8964P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1711
_refine_ls_number_parameters     100
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.0214(4) 1.14653(16) 0.19511(6) 0.0384(4) Uani 1 1 d . . . . .
N1 N 0.3130(5) 0.8584(2) 0.06650(8) 0.0261(4) Uani 1 1 d . . . . .
C1 C 0.2444(5) 1.0063(2) 0.09970(9) 0.0231(4) Uani 1 1 d . . . . .
F2 F 0.0032(4) 0.52671(17) 0.17878(7) 0.0474(4) Uani 1 1 d . . . . .
N2 N 0.3396(6) 1.1617(2) 0.07333(9) 0.0339(4) Uani 1 1 d D . . . .
H2A H 0.426(6) 1.166(3) 0.0342(7) 0.034(7) Uiso 1 1 d D . . . .
H2B H 0.265(7) 1.258(2) 0.0902(12) 0.043(7) Uiso 1 1 d D . . . .
C2 C 0.0861(5) 0.9943(2) 0.16264(9) 0.0246(4) Uani 1 1 d . . . . .
F3 F 0.3072(5) 0.56432(17) 0.05800(7) 0.0486(4) Uani 1 1 d . . . . .
C3 C 0.0029(5) 0.8372(3) 0.19110(9) 0.0278(4) Uani 1 1 d . . . . .
H3 H -0.1015 0.8308 0.2338 0.033 Uiso 1 1 calc R U . . .
C4 C 0.0775(6) 0.6881(3) 0.15495(10) 0.0292(4) Uani 1 1 d . . . . .
C5 C 0.2299(6) 0.7075(3) 0.09389(10) 0.0285(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
F1 C2 1.357(2) . ?
N1 C5 1.315(2) . ?
N1 C1 1.338(2) . ?
C1 N2 1.349(2) . ?
C1 C2 1.409(2) . ?
F2 C4 1.352(2) . ?
N2 H2A 0.857(9) . ?
N2 H2B 0.854(10) . ?
C2 C3 1.366(3) . ?
F3 C5 1.344(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(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
C5 N1 C1 118.69(16) . . ?
N1 C1 N2 119.42(16) . . ?
N1 C1 C2 118.76(16) . . ?
N2 C1 C2 121.79(17) . . ?
C1 N2 H2A 120.2(16) . . ?
C1 N2 H2B 120.6(18) . . ?
H2A N2 H2B 117(2) . . ?
F1 C2 C3 120.37(16) . . ?
F1 C2 C1 117.30(16) . . ?
C3 C2 C1 122.33(17) . . ?
C2 C3 C4 116.89(17) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
F2 C4 C5 120.44(18) . . ?
F2 C4 C3 121.27(18) . . ?
C5 C4 C3 118.29(17) . . ?
N1 C5 F3 115.61(17) . . ?
N1 C5 C4 125.04(18) . . ?
F3 C5 C4 119.35(17) . . ?

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
C5 N1 C1 N2 177.7(2) . . . . ?
C5 N1 C1 C2 0.0(3) . . . . ?
N1 C1 C2 F1 179.76(17) . . . . ?
N2 C1 C2 F1 2.1(3) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
N2 C1 C2 C3 -177.1(2) . . . . ?
F1 C2 C3 C4 -179.90(18) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 F2 -179.68(19) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C1 N1 C5 F3 -179.75(18) . . . . ?
C1 N1 C5 C4 -0.3(3) . . . . ?
F2 C4 C5 N1 -179.8(2) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
F2 C4 C5 F3 -0.4(3) . . . . ?
C3 C4 C5 F3 179.55(19) . . . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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-M46
_database_code_depnum_ccdc_archive 'CCDC 1911497'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-amino-4-chloro-3,5,6-trifluoropyridine
_chemical_name_common            ?
_chemical_melting_point          397
_chemical_formula_moiety         'C5 H2 Cl F3 N2'
_chemical_formula_sum            'C5 H2 Cl F3 N2'
_chemical_formula_weight         182.54

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'
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                   5.0807(5)
_cell_length_b                   7.6319(7)
_cell_length_c                   8.5518(9)
_cell_angle_alpha                77.722(4)
_cell_angle_beta                 89.064(5)
_cell_angle_gamma                87.753(4)
_cell_volume                     323.75(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3259
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.05

_exptl_crystal_description       plate_thick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_F_000             180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.575
_shelx_estimated_absorpt_T_min   0.735
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6162
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5129
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.437
_diffrn_reflns_theta_max         26.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1265
_reflns_number_gt                1038
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0249P)²+0.2336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1265
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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 -0.39428(10) 0.24477(8) 0.47417(7) 0.0564(2) Uani 1 1 d . . . . .
F1 F -0.1342(3) 0.58633(17) 0.34426(16) 0.0560(4) Uani 1 1 d . . . . .
N1 N 0.2653(3) 0.3364(2) 0.11539(19) 0.0408(4) Uani 1 1 d . . . . .
F2 F -0.1332(3) -0.02471(17) 0.31272(18) 0.0657(4) Uani 1 1 d . . . . .
C1 C 0.1681(4) 0.4727(3) 0.1762(2) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.2730(4) 0.6354(3) 0.1278(3) 0.0518(5) Uani 1 1 d . . . . .
H2A H 0.406(5) 0.643(3) 0.060(3) 0.058(7) Uiso 1 1 d . . . . .
H2B H 0.220(5) 0.715(3) 0.170(3) 0.050(7) Uiso 1 1 d . . . . .
F3 F 0.2667(3) 0.04728(18) 0.09748(19) 0.0733(5) Uani 1 1 d . . . . .
C2 C -0.0405(4) 0.4457(3) 0.2867(2) 0.0369(4) Uani 1 1 d . . . . .
C3 C -0.1439(4) 0.2801(3) 0.3364(2) 0.0380(4) Uani 1 1 d . . . . .
C4 C -0.0397(4) 0.1413(3) 0.2712(2) 0.0421(5) Uani 1 1 d . . . . .
C5 C 0.1613(4) 0.1791(3) 0.1629(3) 0.0440(5) 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 C3 1.7093(18) . ?
F1 C2 1.341(2) . ?
N1 C5 1.312(3) . ?
N1 C1 1.333(2) . ?
F2 C4 1.345(2) . ?
C1 N2 1.350(3) . ?
C1 C2 1.400(3) . ?
N2 H2A 0.88(3) . ?
N2 H2B 0.80(3) . ?
F3 C5 1.341(2) . ?
C2 C3 1.368(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.365(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
C5 N1 C1 118.17(16) . . ?
N1 C1 N2 118.69(18) . . ?
N1 C1 C2 119.91(17) . . ?
N2 C1 C2 121.40(19) . . ?
C1 N2 H2A 117.1(16) . . ?
C1 N2 H2B 117.9(18) . . ?
H2A N2 H2B 125(2) . . ?
F1 C2 C3 120.77(17) . . ?
F1 C2 C1 118.16(16) . . ?
C3 C2 C1 121.06(18) . . ?
C2 C3 C4 117.80(17) . . ?
C2 C3 Cl1 121.42(16) . . ?
C4 C3 Cl1 120.78(15) . . ?
F2 C4 C5 121.20(19) . . ?
F2 C4 C3 121.24(17) . . ?
C5 C4 C3 117.56(18) . . ?
N1 C5 F3 115.50(17) . . ?
N1 C5 C4 125.48(18) . . ?
F3 C5 C4 119.02(18) . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_2Fxcr-M16_1
_database_code_depnum_ccdc_archive 'CCDC 1911503'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2-amino-5,7-difluoroquinoline 18-crown-6, associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          391
_chemical_formula_moiety         '2(C9 H6 F2 N3), C12 H24 O6'
_chemical_formula_sum            'C30 H36 F4 N4 O6'
_chemical_formula_weight         624.63

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.6301(5)
_cell_length_b                   8.1303(3)
_cell_length_c                   15.8162(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.549(2)
_cell_angle_gamma                90
_cell_volume                     1556.83(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.560
_exptl_crystal_size_min          0.420
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8688
_exptl_absorpt_correction_T_max  0.9281
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27327
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.829
_diffrn_reflns_theta_max         28.016
_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             3766
_reflns_number_gt                2962
_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-2014/7 (Sheldrick, 2014)'
_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+0.3941P] 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         3766
_refine_ls_number_parameters     207
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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
C1 C 0.20270(10) 0.32882(15) 0.50853(8) 0.0407(3) Uani 1 1 d . . . . .
F1 F 0.54830(8) 0.19279(16) 0.43066(7) 0.0823(3) Uani 1 1 d . . . . .
N1 N 0.28533(9) 0.36983(14) 0.57817(7) 0.0427(3) Uani 1 1 d . . . . .
F2 F 0.66915(8) 0.41666(17) 0.71470(6) 0.0819(3) Uani 1 1 d . . . . .
N2 N 0.09896(10) 0.34285(18) 0.51412(9) 0.0540(3) Uani 1 1 d D . . . .
H2A H 0.0905(15) 0.382(2) 0.5616(8) 0.067(5) Uiso 1 1 d D . . . .
H2B H 0.0441(11) 0.328(2) 0.4692(8) 0.063(5) Uiso 1 1 d D . . . .
C2 C 0.22029(11) 0.26528(17) 0.42910(8) 0.0458(3) Uani 1 1 d . . . . .
H2 H 0.1604 0.2424 0.3806 0.055 Uiso 1 1 calc R U . . .
C3A C 0.41460(11) 0.27879(16) 0.49891(8) 0.0421(3) Uani 1 1 d . . . . .
C3 C 0.32410(12) 0.23888(18) 0.42513(8) 0.0481(3) Uani 1 1 d . . . . .
H3 H 0.3363 0.1949 0.3745 0.058 Uiso 1 1 calc R U . . .
C4 C 0.52605(12) 0.2590(2) 0.50254(9) 0.0530(3) Uani 1 1 d . . . . .
C5 C 0.61198(12) 0.3037(2) 0.57231(10) 0.0592(4) Uani 1 1 d . . . . .
H5 H 0.6850 0.2899 0.5722 0.071 Uiso 1 1 calc R U . . .
C6 C 0.58411(11) 0.3711(2) 0.64385(9) 0.0538(3) Uani 1 1 d . . . . .
C7A C 0.39072(10) 0.34721(15) 0.57382(8) 0.0388(3) Uani 1 1 d . . . . .
C7 C 0.47913(11) 0.39422(19) 0.64704(8) 0.0481(3) Uani 1 1 d . . . . .
H7 H 0.4654 0.4404 0.6967 0.058 Uiso 1 1 calc R U . . .
O1 O 0.03533(8) 0.40846(14) 0.68331(6) 0.0560(3) Uani 1 1 d . . . . .
O2 O 0.11504(8) 0.71654(13) 0.63519(6) 0.0499(2) Uani 1 1 d . . . . .
O3 O 0.12891(8) 0.75111(11) 0.45443(6) 0.0487(2) Uani 1 1 d . . . . .
C8 C 0.06254(12) 0.5474(2) 0.73887(8) 0.0518(3) Uani 1 1 d . . . . .
H8A H 0.0843 0.5131 0.8001 0.062 Uiso 1 1 calc R U . . .
H8B H -0.0011 0.6192 0.7294 0.062 Uiso 1 1 calc R U . . .
C9 C 0.15539(12) 0.6366(2) 0.71828(9) 0.0529(3) Uani 1 1 d . . . . .
H9A H 0.1862 0.7172 0.7639 0.064 Uiso 1 1 calc R U . . .
H9B H 0.2133 0.5596 0.7163 0.064 Uiso 1 1 calc R U . . .
C10 C 0.20285(12) 0.7895(2) 0.60887(10) 0.0563(4) Uani 1 1 d . . . . .
H10A H 0.2559 0.7056 0.6051 0.068 Uiso 1 1 calc R U . . .
H10B H 0.2404 0.8696 0.6526 0.068 Uiso 1 1 calc R U . . .
C11 C 0.15971(13) 0.87175(18) 0.52161(10) 0.0558(4) Uani 1 1 d . . . . .
H11A H 0.0962 0.9389 0.5215 0.067 Uiso 1 1 calc R U . . .
H11B H 0.2161 0.9428 0.5107 0.067 Uiso 1 1 calc R U . . .
C12 C 0.08237(14) 0.8190(2) 0.36992(10) 0.0598(4) Uani 1 1 d . . . . .
H12A H 0.1345 0.8939 0.3555 0.072 Uiso 1 1 calc R U . . .
H12B H 0.0161 0.8803 0.3690 0.072 Uiso 1 1 calc R U . . .
C13 C 0.05478(14) 0.6833(2) 0.30411(10) 0.0604(4) Uani 1 1 d . . . . .
H13A H 0.0352 0.7283 0.2449 0.072 Uiso 1 1 calc R U . . .
H13B H 0.1184 0.6120 0.3113 0.072 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
C1 N1 1.3261(16) . ?
C1 N2 1.3430(17) . ?
C1 C2 1.4331(18) . ?
F1 C4 1.3578(16) . ?
N1 C7A 1.3647(15) . ?
F2 C6 1.3641(16) . ?
N2 H2A 0.850(9) . ?
N2 H2B 0.848(9) . ?
C2 C3 1.3476(19) . ?
C2 H2 0.9300 . ?
C3A C4 1.4016(19) . ?
C3A C7A 1.4170(17) . ?
C3A C3 1.4190(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3543(19) . ?
C7A C7 1.4133(17) . ?
C7 H7 0.9300 . ?
O1 C8 1.4120(18) . ?
O1 C13 1.4213(18) 3_566 ?
O2 C10 1.4207(17) . ?
O2 C9 1.4240(17) . ?
O3 C12 1.4105(17) . ?
O3 C11 1.4166(17) . ?
C8 C9 1.492(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.490(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.489(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O1 1.4213(18) 3_566 ?
C13 H13A 0.9700 . ?
C13 H13B 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
N1 C1 N2 118.41(11) . . ?
N1 C1 C2 122.48(11) . . ?
N2 C1 C2 119.08(12) . . ?
C1 N1 C7A 118.19(10) . . ?
C1 N2 H2A 117.4(12) . . ?
C1 N2 H2B 120.8(12) . . ?
H2A N2 H2B 121.0(17) . . ?
C3 C2 C1 119.61(12) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3A C7A 117.46(12) . . ?
C4 C3A C3 124.88(12) . . ?
C7A C3A C3 117.64(12) . . ?
C2 C3 C3A 119.46(12) . . ?
C2 C3 H3 120.3 . . ?
C3A C3 H3 120.3 . . ?
F1 C4 C5 118.57(13) . . ?
F1 C4 C3A 117.14(13) . . ?
C5 C4 C3A 124.29(13) . . ?
C4 C5 C6 115.96(13) . . ?
C4 C5 H5 122.0 . . ?
C6 C5 H5 122.0 . . ?
C7 C6 F2 118.81(13) . . ?
C7 C6 C5 124.25(13) . . ?
F2 C6 C5 116.94(13) . . ?
N1 C7A C7 118.46(11) . . ?
N1 C7A C3A 122.55(11) . . ?
C7 C7A C3A 118.99(11) . . ?
C6 C7 C7A 119.04(12) . . ?
C6 C7 H7 120.5 . . ?
C7A C7 H7 120.5 . . ?
C8 O1 C13 113.27(11) . 3_566 ?
C10 O2 C9 110.92(11) . . ?
C12 O3 C11 113.01(11) . . ?
O1 C8 C9 108.67(11) . . ?
O1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
O1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
O2 C9 C8 109.05(11) . . ?
O2 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
O2 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
O2 C10 C11 110.42(12) . . ?
O2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
O2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O3 C11 C10 109.51(12) . . ?
O3 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
O3 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
O3 C12 C13 108.87(13) . . ?
O3 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
O3 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
O1 C13 C12 109.17(12) 3_566 . ?
O1 C13 H13A 109.8 3_566 . ?
C12 C13 H13A 109.8 . . ?
O1 C13 H13B 109.8 3_566 . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?

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
N2 C1 N1 C7A 176.62(12) . . . . ?
C2 C1 N1 C7A -1.26(19) . . . . ?
N1 C1 C2 C3 2.9(2) . . . . ?
N2 C1 C2 C3 -174.98(13) . . . . ?
C1 C2 C3 C3A -1.8(2) . . . . ?
C4 C3A C3 C2 -179.19(14) . . . . ?
C7A C3A C3 C2 -0.7(2) . . . . ?
C7A C3A C4 F1 179.74(13) . . . . ?
C3 C3A C4 F1 -1.8(2) . . . . ?
C7A C3A C4 C5 -1.2(2) . . . . ?
C3 C3A C4 C5 177.33(15) . . . . ?
F1 C4 C5 C6 179.85(15) . . . . ?
C3A C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C4 C5 C6 F2 179.94(15) . . . . ?
C1 N1 C7A C7 178.56(12) . . . . ?
C1 N1 C7A C3A -1.38(18) . . . . ?
C4 C3A C7A N1 -179.02(12) . . . . ?
C3 C3A C7A N1 2.39(19) . . . . ?
C4 C3A C7A C7 1.04(19) . . . . ?
C3 C3A C7A C7 -177.55(12) . . . . ?
F2 C6 C7 C7A -179.98(13) . . . . ?
C5 C6 C7 C7A 0.2(2) . . . . ?
N1 C7A C7 C6 179.44(13) . . . . ?
C3A C7A C7 C6 -0.6(2) . . . . ?
C13 O1 C8 C9 -178.35(12) 3_566 . . . ?
C10 O2 C9 C8 -174.20(12) . . . . ?
O1 C8 C9 O2 72.22(15) . . . . ?
C9 O2 C10 C11 179.61(12) . . . . ?
C12 O3 C11 C10 177.27(12) . . . . ?
O2 C10 C11 O3 -73.13(16) . . . . ?
C11 O3 C12 C13 179.01(12) . . . . ?
O3 C12 C13 O1 69.69(16) . . . 3_566 ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_2Hxcr-m9882
_database_code_depnum_ccdc_archive 'CCDC 1911505'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
N4-[(9-anthracenyl)methyl]-2,4-diamino-3,5,6-trifluoropyridine 18-crown-6, 
associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          427
_chemical_formula_moiety         '2(C20 H14 F3 N3), C12 H24 O6'
_chemical_formula_sum            'C52 H52 F6 N6 O6'
_chemical_formula_weight         970.99

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           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                   15.8794(6)
_cell_length_b                   13.2887(6)
_cell_length_c                   11.5020(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.930(2)
_cell_angle_gamma                90
_cell_volume                     2397.69(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9795
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.83

_exptl_crystal_description       block
_exptl_crystal_colour            bronze
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.370
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8706
_exptl_absorpt_correction_T_max  0.9255
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48173
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.298
_diffrn_reflns_theta_max         27.886
_diffrn_reflns_theta_full        25.242
_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             5726
_reflns_number_gt                4296
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0579P)²+0.9275P] 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         5726
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.23273(7) 0.39844(9) 1.01233(8) 0.0669(3) Uani 1 1 d . . . . .
N1 N 0.12034(8) 0.51728(10) 0.75388(11) 0.0460(3) Uani 1 1 d . . . . .
C1 C 0.14313(9) 0.48793(10) 0.86623(12) 0.0379(3) Uani 1 1 d . . . . .
F2 F 0.27719(7) 0.38796(8) 0.61411(8) 0.0630(3) Uani 1 1 d . . . . .
N2 N 0.09978(10) 0.52513(12) 0.94820(13) 0.0534(4) Uani 1 1 d . . . . .
H2A H 0.0575(13) 0.5630(15) 0.9251(17) 0.059(5) Uiso 1 1 d . . . . .
H2B H 0.1112(13) 0.5029(14) 1.020(2) 0.064(6) Uiso 1 1 d . . . . .
C2 C 0.21260(9) 0.42321(11) 0.89682(11) 0.0380(3) Uani 1 1 d . . . . .
F3 F 0.14119(9) 0.51198(10) 0.56490(9) 0.0809(4) Uani 1 1 d . . . . .
C3 C 0.26126(8) 0.38768(10) 0.81560(12) 0.0365(3) Uani 1 1 d . . . . .
N3 N 0.33202(9) 0.32799(12) 0.83898(13) 0.0555(4) Uani 1 1 d . . . . .
H3 H 0.3525(13) 0.3094(15) 0.7767(18) 0.065(6) Uiso 1 1 d . . . . .
C4 C 0.23443(9) 0.42086(11) 0.70070(12) 0.0409(3) Uani 1 1 d . . . . .
C5 C 0.16634(11) 0.48306(12) 0.67736(13) 0.0466(4) Uani 1 1 d . . . . .
C6 C 0.35939(11) 0.27220(15) 0.94708(16) 0.0584(5) Uani 1 1 d . . . . .
H6A H 0.3146 0.2265 0.9619 0.070 Uiso 1 1 calc R U . . .
H6B H 0.3708 0.3184 1.0129 0.070 Uiso 1 1 calc R U . . .
C7 C 0.35219(12) 0.08106(16) 0.8188(2) 0.0692(5) Uani 1 1 d . . . . .
H7 H 0.3024 0.1168 0.8231 0.083 Uiso 1 1 calc R U . . .
C8 C 0.34713(16) -0.00722(19) 0.7606(2) 0.0849(7) Uani 1 1 d . . . . .
H8 H 0.2943 -0.0306 0.7245 0.102 Uiso 1 1 calc R U . . .
C9 C 0.42088(18) -0.06473(19) 0.7535(2) 0.0894(7) Uani 1 1 d . . . . .
H9 H 0.4165 -0.1261 0.7142 0.107 Uiso 1 1 calc R U . . .
C10A C 0.50651(11) 0.06360(14) 0.86453(17) 0.0561(4) Uani 1 1 d . . . . .
C10 C 0.49750(15) -0.03030(17) 0.8041(2) 0.0787(6) Uani 1 1 d . . . . .
H10 H 0.5458 -0.0688 0.7996 0.094 Uiso 1 1 calc R U . . .
C11 C 0.67609(14) 0.2324(2) 1.0195(3) 0.0936(8) Uani 1 1 d . . . . .
H11 H 0.7246 0.1954 1.0116 0.112 Uiso 1 1 calc R U . . .
C12 C 0.6845(2) 0.3211(2) 1.0759(3) 0.1142(11) Uani 1 1 d . . . . .
H12 H 0.7384 0.3449 1.1068 0.137 Uiso 1 1 calc R U . . .
C13 C 0.6122(2) 0.3776(2) 1.0881(3) 0.1082(9) Uani 1 1 d . . . . .
H13 H 0.6188 0.4391 1.1272 0.130 Uiso 1 1 calc R U . . .
C14A C 0.51993(11) 0.25113(13) 0.98372(15) 0.0557(4) Uani 1 1 d . . . . .
C14 C 0.53317(17) 0.34533(17) 1.0447(2) 0.0797(6) Uani 1 1 d . . . . .
H14 H 0.4864 0.3848 1.0545 0.096 Uiso 1 1 calc R U . . .
C15 C 0.43923(10) 0.21336(13) 0.93537(15) 0.0508(4) Uani 1 1 d . . . . .
C15A C 0.43154(10) 0.12120(13) 0.87388(15) 0.0505(4) Uani 1 1 d . . . . .
C16A C 0.59407(11) 0.19347(15) 0.97135(18) 0.0622(5) Uani 1 1 d . . . . .
C16 C 0.58508(11) 0.10190(15) 0.91412(19) 0.0662(5) Uani 1 1 d . . . . .
H16 H 0.6337 0.0644 0.9086 0.079 Uiso 1 1 calc R U . . .
O1 O 0.03959(8) 0.68147(9) 1.12216(11) 0.0597(3) Uani 1 1 d . . . . .
O2 O -0.03959(8) 0.68021(9) 0.87973(11) 0.0587(3) Uani 1 1 d . . . . .
O3 O -0.11905(8) 0.50198(10) 0.78189(10) 0.0585(3) Uani 1 1 d . . . . .
C17 C 0.04016(13) 0.76275(13) 1.0434(2) 0.0687(5) Uani 1 1 d . . . . .
H17A H 0.0886 0.7567 1.0018 0.082 Uiso 1 1 calc R U . . .
H17B H 0.0454 0.8256 1.0868 0.082 Uiso 1 1 calc R U . . .
C18 C -0.04019(13) 0.76273(13) 0.95769(19) 0.0669(5) Uani 1 1 d . . . . .
H18A H -0.0887 0.7574 0.9992 0.080 Uiso 1 1 calc R U . . .
H18B H -0.0452 0.8252 0.9135 0.080 Uiso 1 1 calc R U . . .
C19 C -0.10994(12) 0.68026(16) 0.78781(16) 0.0635(5) Uani 1 1 d . . . . .
H19A H -0.1085 0.7400 0.7397 0.076 Uiso 1 1 calc R U . . .
H19B H -0.1627 0.6806 0.8204 0.076 Uiso 1 1 calc R U . . .
C20 C -0.10548(12) 0.58860(17) 0.71502(14) 0.0643(5) Uani 1 1 d . . . . .
H20A H -0.1485 0.5920 0.6454 0.077 Uiso 1 1 calc R U . . .
H20B H -0.0500 0.5846 0.6899 0.077 Uiso 1 1 calc R U . . .
C21 C -0.11125(15) 0.41207(18) 0.71778(16) 0.0744(6) Uani 1 1 d . . . . .
H21A H -0.0574 0.4121 0.6879 0.089 Uiso 1 1 calc R U . . .
H21B H -0.1569 0.4084 0.6512 0.089 Uiso 1 1 calc R U . . .
C22 C -0.11543(14) 0.32360(17) 0.79517(19) 0.0740(6) Uani 1 1 d . . . . .
H22A H -0.1643 0.3296 0.8360 0.089 Uiso 1 1 calc R U . . .
H22B H -0.1219 0.2626 0.7483 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.3580(16) . ?
N1 C5 1.310(2) . ?
N1 C1 1.3445(18) . ?
C1 N2 1.3450(18) . ?
C1 C2 1.4000(19) . ?
F2 C4 1.3616(15) . ?
N2 H2A 0.85(2) . ?
N2 H2B 0.87(2) . ?
C2 C3 1.3844(18) . ?
F3 C5 1.3491(17) . ?
C3 N3 1.3676(18) . ?
C3 C4 1.396(2) . ?
N3 C6 1.455(2) . ?
N3 H3 0.87(2) . ?
C4 C5 1.354(2) . ?
C6 C15 1.513(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.347(3) . ?
C7 C15A 1.423(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.411(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.345(3) . ?
C9 H9 0.9300 . ?
C10A C16 1.386(3) . ?
C10A C10 1.425(3) . ?
C10A C15A 1.433(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.342(4) . ?
C11 C16A 1.431(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.346(4) . ?
C13 H13 0.9300 . ?
C14A C15 1.408(2) . ?
C14A C16A 1.430(2) . ?
C14A C14 1.434(3) . ?
C14 H14 0.9300 . ?
C15 C15A 1.410(2) . ?
C16A C16 1.380(3) . ?
C16 H16 0.9300 . ?
O1 C17 1.411(2) . ?
O1 C22 1.415(2) 3_567 ?
O2 C19 1.414(2) . ?
O2 C18 1.418(2) . ?
O3 C20 1.419(2) . ?
O3 C21 1.419(2) . ?
C17 C18 1.486(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.486(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.482(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O1 1.415(2) 3_567 ?
C22 H22A 0.9700 . ?
C22 H22B 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
C5 N1 C1 116.76(12) . . ?
N1 C1 N2 118.45(13) . . ?
N1 C1 C2 120.26(12) . . ?
N2 C1 C2 121.25(13) . . ?
C1 N2 H2A 117.7(13) . . ?
C1 N2 H2B 119.1(13) . . ?
H2A N2 H2B 122.5(19) . . ?
F1 C2 C3 120.42(12) . . ?
F1 C2 C1 116.83(12) . . ?
C3 C2 C1 122.71(12) . . ?
N3 C3 C2 126.35(13) . . ?
N3 C3 C4 119.35(12) . . ?
C2 C3 C4 114.27(12) . . ?
C3 N3 C6 126.22(13) . . ?
C3 N3 H3 113.9(13) . . ?
C6 N3 H3 117.4(13) . . ?
C5 C4 F2 121.63(13) . . ?
C5 C4 C3 119.83(12) . . ?
F2 C4 C3 118.53(13) . . ?
N1 C5 F3 115.62(13) . . ?
N1 C5 C4 126.17(13) . . ?
F3 C5 C4 118.19(13) . . ?
N3 C6 C15 109.30(13) . . ?
N3 C6 H6A 109.8 . . ?
C15 C6 H6A 109.8 . . ?
N3 C6 H6B 109.8 . . ?
C15 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 C15A 121.88(19) . . ?
C8 C7 H7 119.1 . . ?
C15A C7 H7 119.1 . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C16 C10A C10 122.57(17) . . ?
C16 C10A C15A 118.57(17) . . ?
C10 C10A C15A 118.86(17) . . ?
C9 C10 C10A 121.6(2) . . ?
C9 C10 H10 119.2 . . ?
C10A C10 H10 119.2 . . ?
C12 C11 C16A 121.4(2) . . ?
C12 C11 H11 119.3 . . ?
C16A C11 H11 119.3 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14A C16A 118.85(17) . . ?
C15 C14A C14 124.03(17) . . ?
C16A C14A C14 117.11(18) . . ?
C13 C14 C14A 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C14A C14 H14 119.4 . . ?
C14A C15 C15A 120.69(14) . . ?
C14A C15 C6 120.29(17) . . ?
C15A C15 C6 119.01(16) . . ?
C15 C15A C7 123.41(16) . . ?
C15 C15A C10A 119.55(15) . . ?
C7 C15A C10A 117.04(17) . . ?
C16 C16A C11 121.60(19) . . ?
C16 C16A C14A 119.60(17) . . ?
C11 C16A C14A 118.8(2) . . ?
C16A C16 C10A 122.68(16) . . ?
C16A C16 H16 118.7 . . ?
C10A C16 H16 118.7 . . ?
C17 O1 C22 112.23(16) . 3_567 ?
C19 O2 C18 112.99(14) . . ?
C20 O3 C21 111.61(14) . . ?
O1 C17 C18 109.60(15) . . ?
O1 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O1 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O2 C18 C17 109.28(14) . . ?
O2 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
O2 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
O2 C19 C20 108.65(13) . . ?
O2 C19 H19A 110.0 . . ?
C20 C19 H19A 110.0 . . ?
O2 C19 H19B 110.0 . . ?
C20 C19 H19B 110.0 . . ?
H19A C19 H19B 108.3 . . ?
O3 C20 C19 109.57(13) . . ?
O3 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
O3 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
O3 C21 C22 109.88(15) . . ?
O3 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
O3 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
O1 C22 C21 109.17(17) 3_567 . ?
O1 C22 H22A 109.8 3_567 . ?
C21 C22 H22A 109.8 . . ?
O1 C22 H22B 109.8 3_567 . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.3 . . ?

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
C5 N1 C1 N2 177.05(15) . . . . ?
C5 N1 C1 C2 -0.5(2) . . . . ?
N1 C1 C2 F1 178.79(13) . . . . ?
N2 C1 C2 F1 1.3(2) . . . . ?
N1 C1 C2 C3 0.9(2) . . . . ?
N2 C1 C2 C3 -176.62(15) . . . . ?
F1 C2 C3 N3 -0.9(2) . . . . ?
C1 C2 C3 N3 177.00(15) . . . . ?
F1 C2 C3 C4 -178.65(13) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 N3 C6 14.5(3) . . . . ?
C4 C3 N3 C6 -167.84(17) . . . . ?
N3 C3 C4 C5 -177.52(15) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
N3 C3 C4 F2 3.5(2) . . . . ?
C2 C3 C4 F2 -178.50(13) . . . . ?
C1 N1 C5 F3 178.75(14) . . . . ?
C1 N1 C5 C4 0.2(3) . . . . ?
F2 C4 C5 N1 178.75(15) . . . . ?
C3 C4 C5 N1 -0.1(3) . . . . ?
F2 C4 C5 F3 0.2(2) . . . . ?
C3 C4 C5 F3 -178.70(14) . . . . ?
C3 N3 C6 C15 178.29(16) . . . . ?
C15A C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C8 C9 C10 C10A -0.4(4) . . . . ?
C16 C10A C10 C9 -178.0(2) . . . . ?
C15A C10A C10 C9 1.6(3) . . . . ?
C16A C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C14A -0.1(5) . . . . ?
C15 C14A C14 C13 -179.4(2) . . . . ?
C16A C14A C14 C13 0.1(3) . . . . ?
C16A C14A C15 C15A -1.2(2) . . . . ?
C14 C14A C15 C15A 178.32(17) . . . . ?
C16A C14A C15 C6 179.84(16) . . . . ?
C14 C14A C15 C6 -0.7(3) . . . . ?
N3 C6 C15 C14A 98.6(2) . . . . ?
N3 C6 C15 C15A -80.4(2) . . . . ?
C14A C15 C15A C7 -177.28(17) . . . . ?
C6 C15 C15A C7 1.7(2) . . . . ?
C14A C15 C15A C10A 2.4(2) . . . . ?
C6 C15 C15A C10A -178.55(15) . . . . ?
C8 C7 C15A C15 179.9(2) . . . . ?
C8 C7 C15A C10A 0.2(3) . . . . ?
C16 C10A C15A C15 -1.6(3) . . . . ?
C10 C10A C15A C15 178.76(18) . . . . ?
C16 C10A C15A C7 178.11(18) . . . . ?
C10 C10A C15A C7 -1.5(3) . . . . ?
C12 C11 C16A C16 -179.5(3) . . . . ?
C12 C11 C16A C14A 0.2(4) . . . . ?
C15 C14A C16A C16 -0.9(3) . . . . ?
C14 C14A C16A C16 179.57(19) . . . . ?
C15 C14A C16A C11 179.40(19) . . . . ?
C14 C14A C16A C11 -0.1(3) . . . . ?
C11 C16A C16 C10A -178.6(2) . . . . ?
C14A C16A C16 C10A 1.7(3) . . . . ?
C10 C10A C16 C16A 179.1(2) . . . . ?
C15A C10A C16 C16A -0.5(3) . . . . ?
C22 O1 C17 C18 178.89(15) 3_567 . . . ?
C19 O2 C18 C17 -174.03(15) . . . . ?
O1 C17 C18 O2 -70.60(19) . . . . ?
C18 O2 C19 C20 -177.28(15) . . . . ?
C21 O3 C20 C19 -177.14(15) . . . . ?
O2 C19 C20 O3 67.35(18) . . . . ?
C20 O3 C21 C22 173.19(16) . . . . ?
O3 C21 C22 O1 -71.2(2) . . . 3_567 ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_H-m72
_database_code_depnum_ccdc_archive 'CCDC 1911498'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
N4-[(9-anthracenyl)methyl]-2,4-diamino-3,5,6-trifluoropyridine
;
_chemical_name_common            ?
_chemical_melting_point          490
_chemical_formula_moiety         'C20 H14 F3 N3'
_chemical_formula_sum            'C20 H14 F3 N3'
_chemical_formula_weight         353.34

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      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                   8.5190(8)
_cell_length_b                   12.8724(13)
_cell_length_c                   15.6110(17)
_cell_angle_alpha                110.573(4)
_cell_angle_beta                 98.064(4)
_cell_angle_gamma                90.097(4)
_cell_volume                     1584.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5775
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8229
_exptl_absorpt_correction_T_max  0.9773
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26270
_diffrn_reflns_av_unetI/netI     0.0984
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.692
_diffrn_reflns_theta_max         25.116
_diffrn_reflns_theta_full        25.116
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5628
_reflns_number_gt                2580
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1600P)²] 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         5628
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.0978
_refine_ls_wR_factor_ref         0.2623
_refine_ls_wR_factor_gt          0.2388
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_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 0.8691(3) 0.4205(2) 0.89997(18) 0.0612(8) Uani 1 1 d . . . . .
N1 N 0.7289(5) 0.6374(3) 0.8180(3) 0.0491(10) Uani 1 1 d . . . . .
C1 C 0.8094(6) 0.5841(4) 0.8690(3) 0.0482(12) Uani 1 1 d . . . . .
F2 F 0.4767(3) 0.41092(19) 0.64869(18) 0.0527(7) Uani 1 1 d . . . . .
C2 C 0.7804(5) 0.4716(3) 0.8480(3) 0.0375(10) Uani 1 1 d . . . . .
N2 N 0.9141(5) 0.6466(3) 0.9432(3) 0.0658(12) Uani 1 1 d . . . . .
H2A H 0.9264 0.7170 0.9558 0.079 Uiso 1 1 calc R U . . .
H2B H 0.9682 0.6158 0.9777 0.079 Uiso 1 1 calc R U . . .
F3 F 0.5428(3) 0.6269(2) 0.6966(2) 0.0657(9) Uani 1 1 d . . . . .
N3 N 0.6599(5) 0.2931(3) 0.7553(3) 0.0512(11) Uani 1 1 d . . . . .
H3 H 0.7261 0.2658 0.7874 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6751(5) 0.4044(3) 0.7736(3) 0.0382(10) Uani 1 1 d . . . . .
C4 C 0.5875(5) 0.4629(3) 0.7230(3) 0.0415(11) Uani 1 1 d . . . . .
C5 C 0.6258(6) 0.5764(4) 0.7509(3) 0.0443(12) Uani 1 1 d . . . . .
C6 C 0.5393(6) 0.2157(3) 0.6849(3) 0.0499(12) Uani 1 1 d . . . . .
H6A H 0.5607 0.2074 0.6235 0.060 Uiso 1 1 calc R U . . .
H6B H 0.4349 0.2446 0.6916 0.060 Uiso 1 1 calc R U . . .
C7 C 0.6874(6) 0.0191(5) 0.5616(3) 0.0617(14) Uani 1 1 d . . . . .
H7 H 0.6947 0.0864 0.5523 0.074 Uiso 1 1 calc R U . . .
C8 C 0.7520(6) -0.0723(6) 0.5042(4) 0.0737(18) Uani 1 1 d . . . . .
H8 H 0.8040 -0.0663 0.4575 0.088 Uiso 1 1 calc R U . . .
C9 C 0.7390(7) -0.1762(5) 0.5167(4) 0.0740(17) Uani 1 1 d . . . . .
H9 H 0.7807 -0.2385 0.4771 0.089 Uiso 1 1 calc R U . . .
C10A C 0.6034(5) -0.0917(3) 0.6465(3) 0.0357(10) Uani 1 1 d . . . . .
C10 C 0.6688(6) -0.1846(4) 0.5834(4) 0.0669(16) Uani 1 1 d . . . . .
H10 H 0.6611 -0.2534 0.5900 0.080 Uiso 1 1 calc R U . . .
C11 C 0.4131(7) -0.0203(5) 0.8606(4) 0.0671(16) Uani 1 1 d . . . . .
H11 H 0.4117 -0.0871 0.8711 0.081 Uiso 1 1 calc R U . . .
C12 C 0.3531(7) 0.0704(7) 0.9186(4) 0.087(2) Uani 1 1 d . . . . .
H12 H 0.3152 0.0647 0.9699 0.104 Uiso 1 1 calc R U . . .
C13 C 0.3453(7) 0.1701(6) 0.9055(5) 0.0830(19) Uani 1 1 d . . . . .
H13 H 0.2995 0.2302 0.9451 0.100 Uiso 1 1 calc R U . . .
C14A C 0.4771(5) 0.0904(3) 0.7686(3) 0.0391(11) Uani 1 1 d . . . . .
C14 C 0.4067(6) 0.1774(4) 0.8330(4) 0.0576(13) Uani 1 1 d . . . . .
H14 H 0.4025 0.2453 0.8243 0.069 Uiso 1 1 calc R U . . .
C15 C 0.5432(5) 0.1073(3) 0.6965(3) 0.0342(10) Uani 1 1 d . . . . .
C15A C 0.6100(5) 0.0134(4) 0.6346(3) 0.0424(11) Uani 1 1 d . . . . .
C16A C 0.4792(5) -0.0133(4) 0.7824(3) 0.0502(12) Uani 1 1 d . . . . .
C16 C 0.5393(6) -0.1015(4) 0.7201(4) 0.0582(14) Uani 1 1 d . . . . .
H16 H 0.5370 -0.1702 0.7274 0.070 Uiso 1 1 calc R U . . .
F4 F -0.1559(4) 0.9205(2) 0.9009(2) 0.0673(9) Uani 1 1 d . . . . .
N4 N -0.0657(5) 1.1334(3) 0.8133(3) 0.0503(10) Uani 1 1 d . . . . .
F5 F 0.1007(3) 0.9078(2) 0.64712(18) 0.0556(8) Uani 1 1 d . . . . .
N5 N -0.1832(5) 1.1456(4) 0.9406(3) 0.0709(13) Uani 1 1 d . . . . .
H5A H -0.1913 1.2155 0.9517 0.085 Uiso 1 1 calc R U . . .
H5B H -0.2173 1.1157 0.9764 0.085 Uiso 1 1 calc R U . . .
F6 F 0.0555(4) 1.1224(2) 0.6917(2) 0.0690(9) Uani 1 1 d . . . . .
N6 N -0.0233(5) 0.7909(3) 0.7550(3) 0.0537(11) Uani 1 1 d . . . . .
H6 H -0.0729 0.7639 0.7875 0.064 Uiso 1 1 calc R U . . .
C17 C -0.1167(5) 1.0822(4) 0.8666(3) 0.0485(12) Uani 1 1 d . . . . .
C18 C -0.0985(5) 0.9694(3) 0.8469(3) 0.0420(11) Uani 1 1 d . . . . .
C19 C -0.0289(5) 0.9030(3) 0.7727(3) 0.0394(11) Uani 1 1 d . . . . .
C20 C 0.0274(5) 0.9592(3) 0.7213(3) 0.0410(11) Uani 1 1 d . . . . .
C21 C 0.0038(6) 1.0714(3) 0.7458(3) 0.0463(12) Uani 1 1 d . . . . .
C22 C 0.0599(6) 0.7142(3) 0.6855(4) 0.0561(14) Uani 1 1 d . . . . .
H22A H 0.1688 0.7422 0.6935 0.067 Uiso 1 1 calc R U . . .
H22B H 0.0090 0.7078 0.6241 0.067 Uiso 1 1 calc R U . . .
C23 C -0.1575(7) 0.5224(5) 0.5602(4) 0.0708(16) Uani 1 1 d . . . . .
H23 H -0.1691 0.5898 0.5511 0.085 Uiso 1 1 calc R U . . .
C24 C -0.2537(7) 0.4267(7) 0.5019(4) 0.087(2) Uani 1 1 d . . . . .
H24 H -0.3303 0.4320 0.4551 0.104 Uiso 1 1 calc R U . . .
C25 C -0.2344(9) 0.3239(6) 0.5141(5) 0.096(2) Uani 1 1 d . . . . .
H25 H -0.2970 0.2617 0.4746 0.115 Uiso 1 1 calc R U . . .
C26A C -0.0338(5) 0.4064(3) 0.6438(3) 0.0396(11) Uani 1 1 d . . . . .
C26 C -0.1274(9) 0.3151(5) 0.5816(5) 0.093(2) Uani 1 1 d . . . . .
H26 H -0.1148 0.2460 0.5874 0.111 Uiso 1 1 calc R U . . .
C27 C 0.2646(8) 0.4766(6) 0.8628(5) 0.086(2) Uani 1 1 d . . . . .
H27 H 0.2687 0.4107 0.8747 0.103 Uiso 1 1 calc R U . . .
C28 C 0.3554(9) 0.5692(9) 0.9216(5) 0.111(3) Uani 1 1 d . . . . .
H28 H 0.4166 0.5650 0.9744 0.133 Uiso 1 1 calc R U . . .
C29 C 0.3597(9) 0.6656(7) 0.9063(6) 0.104(3) Uani 1 1 d . . . . .
H29 H 0.4280 0.7250 0.9451 0.124 Uiso 1 1 calc R U . . .
C30A C 0.1603(6) 0.5867(4) 0.7681(3) 0.0473(12) Uani 1 1 d . . . . .
C30 C 0.2640(7) 0.6737(6) 0.8341(4) 0.0771(18) Uani 1 1 d . . . . .
H30 H 0.2648 0.7420 0.8262 0.092 Uiso 1 1 calc R U . . .
C31 C 0.0575(5) 0.6032(3) 0.6950(3) 0.0363(10) Uani 1 1 d . . . . .
C31A C -0.0410(5) 0.5137(4) 0.6342(3) 0.0440(11) Uani 1 1 d . . . . .
C32A C 0.1613(7) 0.4820(5) 0.7812(4) 0.0613(15) Uani 1 1 d . . . . .
C32 C 0.0686(7) 0.3966(5) 0.7185(4) 0.0705(18) Uani 1 1 d . . . . .
H32 H 0.0731 0.3276 0.7251 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.366(5) . ?
N1 C5 1.284(6) . ?
N1 C1 1.344(6) . ?
C1 N2 1.355(6) . ?
C1 C2 1.382(6) . ?
F2 C4 1.353(5) . ?
C2 C3 1.379(6) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
F3 C5 1.364(5) . ?
N3 C3 1.360(5) . ?
N3 C6 1.472(6) . ?
N3 H3 0.8600 . ?
C3 C4 1.416(6) . ?
C4 C5 1.394(6) . ?
C6 C15 1.468(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.375(8) . ?
C7 C15A 1.418(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.424(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.306(8) . ?
C9 H9 0.9300 . ?
C10A C16 1.384(6) . ?
C10A C10 1.428(6) . ?
C10A C15A 1.430(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.354(9) . ?
C11 C16A 1.445(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.343(8) . ?
C13 H13 0.9300 . ?
C14A C15 1.407(6) . ?
C14A C14 1.416(7) . ?
C14A C16A 1.425(6) . ?
C14 H14 0.9300 . ?
C15 C15A 1.434(6) . ?
C16A C16 1.365(7) . ?
C16 H16 0.9300 . ?
F4 C18 1.355(5) . ?
N4 C21 1.297(6) . ?
N4 C17 1.343(6) . ?
F5 C20 1.355(5) . ?
N5 C17 1.358(6) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
F6 C21 1.353(5) . ?
N6 C19 1.372(5) . ?
N6 C22 1.456(6) . ?
N6 H6 0.8600 . ?
C17 C18 1.388(6) . ?
C18 C19 1.387(6) . ?
C19 C20 1.382(6) . ?
C20 C21 1.381(6) . ?
C22 C31 1.488(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.420(9) . ?
C23 C31A 1.450(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.408(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.331(10) . ?
C25 H25 0.9300 . ?
C26A C26 1.391(8) . ?
C26A C32 1.398(8) . ?
C26A C31A 1.441(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.375(11) . ?
C27 C32A 1.466(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.346(12) . ?
C28 H28 0.9300 . ?
C29 C30 1.331(9) . ?
C29 H29 0.9300 . ?
C30A C31 1.415(7) . ?
C30A C32A 1.432(7) . ?
C30A C30 1.423(8) . ?
C30 H30 0.9300 . ?
C31 C31A 1.392(6) . ?
C32A C32 1.348(8) . ?
C32 H32 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
C5 N1 C1 115.1(4) . . ?
N1 C1 N2 116.9(4) . . ?
N1 C1 C2 120.8(4) . . ?
N2 C1 C2 122.2(5) . . ?
C3 C2 F1 116.7(3) . . ?
C3 C2 C1 124.5(4) . . ?
F1 C2 C1 118.6(4) . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C3 N3 C6 125.3(4) . . ?
C3 N3 H3 117.3 . . ?
C6 N3 H3 117.3 . . ?
C2 C3 N3 120.7(4) . . ?
C2 C3 C4 113.6(4) . . ?
N3 C3 C4 125.7(4) . . ?
F2 C4 C5 121.3(4) . . ?
F2 C4 C3 122.0(4) . . ?
C5 C4 C3 116.7(4) . . ?
N1 C5 F3 117.0(4) . . ?
N1 C5 C4 129.1(4) . . ?
F3 C5 C4 113.9(4) . . ?
N3 C6 C15 109.2(4) . . ?
N3 C6 H6A 109.8 . . ?
C15 C6 H6A 109.8 . . ?
N3 C6 H6B 109.8 . . ?
C15 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 C15A 121.6(5) . . ?
C8 C7 H7 119.2 . . ?
C15A C7 H7 119.2 . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.4(5) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C16 C10A C10 120.8(4) . . ?
C16 C10A C15A 120.1(4) . . ?
C10 C10A C15A 119.1(4) . . ?
C9 C10 C10A 122.2(6) . . ?
C9 C10 H10 118.9 . . ?
C10A C10 H10 118.9 . . ?
C12 C11 C16A 119.9(5) . . ?
C12 C11 H11 120.1 . . ?
C16A C11 H11 120.1 . . ?
C11 C12 C13 123.4(6) . . ?
C11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C14 C13 C12 117.1(6) . . ?
C14 C13 H13 121.5 . . ?
C12 C13 H13 121.5 . . ?
C15 C14A C14 121.3(4) . . ?
C15 C14A C16A 122.6(4) . . ?
C14 C14A C16A 116.1(4) . . ?
C13 C14 C14A 125.5(5) . . ?
C13 C14 H14 117.2 . . ?
C14A C14 H14 117.2 . . ?
C14A C15 C15A 116.7(4) . . ?
C14A C15 C6 121.0(4) . . ?
C15A C15 C6 122.3(4) . . ?
C15 C15A C7 123.1(4) . . ?
C15 C15A C10A 119.9(4) . . ?
C7 C15A C10A 117.0(4) . . ?
C16 C16A C14A 118.7(4) . . ?
C16 C16A C11 123.3(5) . . ?
C14A C16A C11 118.0(5) . . ?
C16A C16 C10A 121.8(4) . . ?
C16A C16 H16 119.1 . . ?
C10A C16 H16 119.1 . . ?
C21 N4 C17 115.5(4) . . ?
C17 N5 H5A 120.0 . . ?
C17 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C19 N6 C22 125.1(4) . . ?
C19 N6 H6 117.5 . . ?
C22 N6 H6 117.5 . . ?
N4 C17 N5 117.3(4) . . ?
N4 C17 C18 120.6(4) . . ?
N5 C17 C18 122.0(5) . . ?
F4 C18 C19 118.0(4) . . ?
F4 C18 C17 118.6(4) . . ?
C19 C18 C17 123.4(4) . . ?
N6 C19 C20 125.9(4) . . ?
N6 C19 C18 119.7(4) . . ?
C20 C19 C18 114.4(4) . . ?
F5 C20 C21 119.2(4) . . ?
F5 C20 C19 122.5(4) . . ?
C21 C20 C19 118.2(4) . . ?
N4 C21 F6 115.9(4) . . ?
N4 C21 C20 127.7(4) . . ?
F6 C21 C20 116.4(4) . . ?
N6 C22 C31 109.6(4) . . ?
N6 C22 H22A 109.8 . . ?
C31 C22 H22A 109.8 . . ?
N6 C22 H22B 109.8 . . ?
C31 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
C24 C23 C31A 119.1(6) . . ?
C24 C23 H23 120.5 . . ?
C31A C23 H23 120.5 . . ?
C25 C24 C23 120.7(6) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.5(7) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C26 C26A C32 120.6(6) . . ?
C26 C26A C31A 121.3(6) . . ?
C32 C26A C31A 118.1(4) . . ?
C25 C26 C26A 121.8(7) . . ?
C25 C26 H26 119.1 . . ?
C26A C26 H26 119.1 . . ?
C28 C27 C32A 119.8(6) . . ?
C28 C27 H27 120.1 . . ?
C32A C27 H27 120.1 . . ?
C29 C28 C27 123.0(7) . . ?
C29 C28 H28 118.5 . . ?
C27 C28 H28 118.5 . . ?
C30 C29 C28 118.4(8) . . ?
C30 C29 H29 120.8 . . ?
C28 C29 H29 120.8 . . ?
C31 C30A C32A 121.5(5) . . ?
C31 C30A C30 122.1(5) . . ?
C32A C30A C30 116.4(5) . . ?
C29 C30 C30A 125.5(7) . . ?
C29 C30 H30 117.2 . . ?
C30A C30 H30 117.2 . . ?
C31A C31 C30A 118.2(4) . . ?
C31A C31 C22 122.7(4) . . ?
C30A C31 C22 119.1(4) . . ?
C31 C31A C26A 120.6(4) . . ?
C31 C31A C23 123.0(5) . . ?
C26A C31A C23 116.4(5) . . ?
C32 C32A C30A 118.2(5) . . ?
C32 C32A C27 125.0(6) . . ?
C30A C32A C27 116.8(6) . . ?
C32A C32 C26A 123.3(5) . . ?
C32A C32 H32 118.3 . . ?
C26A C32 H32 118.3 . . ?

_refine_diff_density_max         1.100
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_2Cxcr-M11_a
_database_code_depnum_ccdc_archive 'CCDC 1911500'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
4-amino-3,5-dichloro-2,6-difluoropyridine 18-crown-6, associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          372
_chemical_formula_moiety         '2(C5 H2 Cl5 F5 N5), C12 H24 O6'
_chemical_formula_sum            'C22 H28 Cl4 F4 N4 O6'
_chemical_formula_weight         662.28

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      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                   19.2435(8)
_cell_length_b                   9.9058(4)
_cell_length_c                   17.6406(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.630(2)
_cell_angle_gamma                90
_cell_volume                     2923.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.97

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.474
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8207
_exptl_absorpt_correction_T_max  0.8622
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30667
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.390
_diffrn_reflns_theta_max         30.207
_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             4345
_reflns_number_gt                3147
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0533P)²+2.9450P] 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         4345
_refine_ls_number_parameters     189
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.990
_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 0.28917(4) 0.58667(6) 0.03284(4) 0.07046(19) Uani 1 1 d . . . . .
F1 F 0.19702(8) 0.41735(17) 0.08608(10) 0.0808(4) Uani 1 1 d . . . . .
N1 N 0.27610(10) 0.2352(2) 0.13023(12) 0.0608(4) Uani 1 1 d . . . . .
C1 C 0.26413(11) 0.3563(2) 0.09734(13) 0.0547(5) Uani 1 1 d . . . . .
O1 O 0.62503(8) 0.53290(16) 0.68530(9) 0.0577(3) Uani 1 1 d . . . . .
Cl2 Cl 0.47901(4) 0.14276(6) 0.13751(5) 0.07258(19) Uani 1 1 d . . . . .
N2 N 0.43334(11) 0.42321(18) 0.06508(14) 0.0579(4) Uani 1 1 d D . . . .
H2A H 0.4788(11) 0.387(2) 0.0785(16) 0.065(7) Uiso 1 1 d D . . . .
H2B H 0.4277(16) 0.5077(18) 0.0522(17) 0.076(8) Uiso 1 1 d D . . . .
F2 F 0.35477(10) 0.05184(15) 0.17456(11) 0.0857(5) Uani 1 1 d . . . . .
O2 O 0.58023(7) 0.69962(14) 0.53975(9) 0.0523(3) Uani 1 1 d . . . . .
C2 C 0.31281(10) 0.42603(19) 0.07478(12) 0.0465(4) Uani 1 1 d . . . . .
O3 O 0.48613(9) 0.69179(15) 0.35609(10) 0.0617(4) Uani 1 1 d . . . . .
C3 C 0.38347(10) 0.36343(18) 0.08678(11) 0.0426(4) Uani 1 1 d . . . . .
C4 C 0.39592(11) 0.23174(19) 0.12089(12) 0.0474(4) Uani 1 1 d . . . . .
C5 C 0.34144(13) 0.1768(2) 0.14088(14) 0.0563(5) Uani 1 1 d . . . . .
C6 C 0.68113(11) 0.5890(2) 0.66429(14) 0.0585(5) Uani 1 1 d . . . . .
H6A H 0.6893 0.5275 0.6266 0.070 Uiso 1 1 calc R U . . .
H6B H 0.7320 0.6016 0.7172 0.070 Uiso 1 1 calc R U . . .
C7 C 0.65186(11) 0.7198(2) 0.61987(14) 0.0583(5) Uani 1 1 d . . . . .
H7A H 0.6419 0.7804 0.6567 0.070 Uiso 1 1 calc R U . . .
H7B H 0.6920 0.7605 0.6091 0.070 Uiso 1 1 calc R U . . .
C8 C 0.55691(14) 0.8175(2) 0.48607(16) 0.0611(5) Uani 1 1 d . . . . .
H8A H 0.5960 0.8374 0.4681 0.073 Uiso 1 1 calc R U . . .
H8B H 0.5539 0.8943 0.5184 0.073 Uiso 1 1 calc R U . . .
C9 C 0.47686(13) 0.7921(2) 0.40764(16) 0.0635(5) Uani 1 1 d . . . . .
H9A H 0.4393 0.7616 0.4256 0.076 Uiso 1 1 calc R U . . .
H9B H 0.4564 0.8746 0.3742 0.076 Uiso 1 1 calc R U . . .
C10 C 0.41623(15) 0.6654(3) 0.27312(15) 0.0705(6) Uani 1 1 d . . . . .
H10A H 0.4313 0.6087 0.2388 0.085 Uiso 1 1 calc R U . . .
H10B H 0.3966 0.7501 0.2422 0.085 Uiso 1 1 calc R U . . .
C11 C 0.35099(13) 0.5990(3) 0.27996(15) 0.0653(6) Uani 1 1 d . . . . .
H11A H 0.3378 0.6515 0.3176 0.078 Uiso 1 1 calc R U . . .
H11B H 0.3037 0.5937 0.2228 0.078 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 C2 1.719(2) . ?
F1 C1 1.349(2) . ?
N1 C1 1.302(3) . ?
N1 C5 1.311(3) . ?
C1 C2 1.372(3) . ?
O1 C11 1.420(3) 5_666 ?
O1 C6 1.417(2) . ?
Cl2 C4 1.7193(19) . ?
N2 C3 1.335(2) . ?
N2 H2A 0.863(16) . ?
N2 H2B 0.860(17) . ?
F2 C5 1.342(3) . ?
O2 C7 1.418(2) . ?
O2 C8 1.429(3) . ?
C2 C3 1.412(2) . ?
O3 C9 1.416(3) . ?
O3 C10 1.440(3) . ?
C3 C4 1.407(3) . ?
C4 C5 1.373(3) . ?
C6 C7 1.474(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.498(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.474(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O1 1.420(3) 5_666 ?
C11 H11A 0.9700 . ?
C11 H11B 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
C1 N1 C5 114.59(17) . . ?
N1 C1 F1 115.10(17) . . ?
N1 C1 C2 126.70(18) . . ?
F1 C1 C2 118.2(2) . . ?
C11 O1 C6 110.28(16) 5_666 . ?
C3 N2 H2A 121.0(17) . . ?
C3 N2 H2B 119.5(18) . . ?
H2A N2 H2B 117(2) . . ?
C7 O2 C8 112.18(16) . . ?
C1 C2 C3 118.70(18) . . ?
C1 C2 Cl1 121.20(15) . . ?
C3 C2 Cl1 120.10(14) . . ?
C9 O3 C10 115.41(18) . . ?
N2 C3 C4 122.65(16) . . ?
N2 C3 C2 122.54(17) . . ?
C4 C3 C2 114.78(16) . . ?
C5 C4 C3 119.14(17) . . ?
C5 C4 Cl2 121.14(16) . . ?
C3 C4 Cl2 119.72(13) . . ?
N1 C5 F2 115.50(18) . . ?
N1 C5 C4 126.1(2) . . ?
F2 C5 C4 118.4(2) . . ?
O1 C6 C7 110.07(16) . . ?
O1 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
O1 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
O2 C7 C6 109.49(16) . . ?
O2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
O2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
O2 C8 C9 108.49(16) . . ?
O2 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
O2 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
O3 C9 C8 108.22(18) . . ?
O3 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
O3 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
O3 C10 C11 113.78(19) . . ?
O3 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
O3 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O1 C11 C10 109.75(19) 5_666 . ?
O1 C11 H11A 109.7 5_666 . ?
C10 C11 H11A 109.7 . . ?
O1 C11 H11B 109.7 5_666 . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?

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
C5 N1 C1 F1 179.99(18) . . . . ?
C5 N1 C1 C2 -0.9(3) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
F1 C1 C2 C3 179.61(17) . . . . ?
N1 C1 C2 Cl1 -179.34(17) . . . . ?
F1 C1 C2 Cl1 -0.3(3) . . . . ?
C1 C2 C3 N2 178.75(19) . . . . ?
Cl1 C2 C3 N2 -1.4(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
Cl1 C2 C3 C4 -179.53(13) . . . . ?
N2 C3 C4 C5 -179.41(19) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
N2 C3 C4 Cl2 1.0(3) . . . . ?
C2 C3 C4 Cl2 179.17(14) . . . . ?
C1 N1 C5 F2 -179.86(18) . . . . ?
C1 N1 C5 C4 0.1(3) . . . . ?
C3 C4 C5 N1 1.0(3) . . . . ?
Cl2 C4 C5 N1 -179.46(17) . . . . ?
C3 C4 C5 F2 -179.04(17) . . . . ?
Cl2 C4 C5 F2 0.5(3) . . . . ?
C11 O1 C6 C7 174.13(17) 5_666 . . . ?
C8 O2 C7 C6 -168.97(17) . . . . ?
O1 C6 C7 O2 -63.2(2) . . . . ?
C7 O2 C8 C9 -174.13(18) . . . . ?
C10 O3 C9 C8 -173.63(18) . . . . ?
O2 C8 C9 O3 -67.5(2) . . . . ?
C9 O3 C10 C11 -69.1(3) . . . . ?
O3 C10 C11 O1 -66.1(3) . . . 5_666 ?

_refine_diff_density_max         0.539
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_2Excr-M18_2
_database_code_depnum_ccdc_archive 'CCDC 1911502'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2-amino-4-chloro-3,5,6-trifluoropyridine 18-crown-6, associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          393
_chemical_formula_moiety         '2(C5 H2 Cl F3 N2), C12 H24 O6'
_chemical_formula_sum            'C22 H28 Cl2 F6 N4 O6'
_chemical_formula_weight         629.38

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      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                   22.3524(11)
_cell_length_b                   8.0294(3)
_cell_length_c                   16.3762(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.214(2)
_cell_angle_gamma                90
_cell_volume                     2775.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.67

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.318
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7874
_exptl_absorpt_correction_T_max  0.8373
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35519
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.930
_diffrn_reflns_theta_max         28.762
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3584
_reflns_number_gt                2658
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0851P)²+2.6871P] 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         3584
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1627
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O1 O 0.25886(6) 0.53682(18) 0.41118(9) 0.0435(3) Uani 1 1 d . . . . .
O2 O 0.34719(7) 0.48537(17) 0.58189(9) 0.0436(3) Uani 1 1 d . . . . .
O3 O 0.31222(7) 0.23142(18) 0.68299(9) 0.0473(3) Uani 1 1 d . . . . .
C6 C 0.31737(9) 0.6241(2) 0.44533(14) 0.0449(5) Uani 1 1 d . . . . .
H6A H 0.3139 0.7330 0.4185 0.054 Uiso 1 1 calc R U . . .
H6B H 0.3508 0.5630 0.4328 0.054 Uiso 1 1 calc R U . . .
C7 C 0.33326(10) 0.6432(2) 0.54083(14) 0.0449(5) Uani 1 1 d . . . . .
H7A H 0.3696 0.7163 0.5630 0.054 Uiso 1 1 calc R U . . .
H7B H 0.2978 0.6933 0.5534 0.054 Uiso 1 1 calc R U . . .
C8 C 0.35526(11) 0.4981(3) 0.67098(14) 0.0504(5) Uani 1 1 d . . . . .
H8A H 0.3173 0.5447 0.6784 0.060 Uiso 1 1 calc R U . . .
H8B H 0.3904 0.5720 0.6988 0.060 Uiso 1 1 calc R U . . .
C9 C 0.36796(11) 0.3303(3) 0.71210(13) 0.0514(5) Uani 1 1 d . . . . .
H9A H 0.4018 0.2764 0.6972 0.062 Uiso 1 1 calc R U . . .
H9B H 0.3813 0.3416 0.7745 0.062 Uiso 1 1 calc R U . . .
C10 C 0.32325(11) 0.0645(3) 0.71176(13) 0.0494(5) Uani 1 1 d . . . . .
H10A H 0.3399 0.0616 0.7744 0.059 Uiso 1 1 calc R U . . .
H10B H 0.3542 0.0139 0.6896 0.059 Uiso 1 1 calc R U . . .
C11 C 0.26262(11) -0.0301(3) 0.68065(14) 0.0483(5) Uani 1 1 d . . . . .
H11A H 0.2690 -0.1421 0.7041 0.058 Uiso 1 1 calc R U . . .
H11B H 0.2310 0.0240 0.7003 0.058 Uiso 1 1 calc R U . . .
Cl1 Cl 0.01184(3) 0.13412(9) 0.60760(5) 0.0732(2) Uani 1 1 d . . . . .
N1 N 0.09858(8) 0.4237(2) 0.44180(11) 0.0467(4) Uani 1 1 d . . . . .
C1 C 0.13614(9) 0.3656(2) 0.51796(13) 0.0394(4) Uani 1 1 d . . . . .
F1 F 0.14628(6) 0.22798(19) 0.64936(8) 0.0567(4) Uani 1 1 d . . . . .
N2 N 0.19918(9) 0.3960(3) 0.54289(15) 0.0522(5) Uani 1 1 d . . . . .
H2B H 0.2113(13) 0.427(4) 0.5029(18) 0.061(8) Uiso 1 1 d . . . . .
H2A H 0.2254(14) 0.336(4) 0.587(2) 0.066(8) Uiso 1 1 d . . . . .
C2 C 0.10889(9) 0.2802(2) 0.57143(12) 0.0395(4) Uani 1 1 d . . . . .
F2 F -0.05521(6) 0.2823(2) 0.43585(11) 0.0729(5) Uani 1 1 d . . . . .
C3 C 0.04482(9) 0.2475(3) 0.54457(14) 0.0433(4) Uani 1 1 d . . . . .
F3 F 0.00236(8) 0.4552(3) 0.34115(10) 0.0797(5) Uani 1 1 d . . . . .
C4 C 0.00807(9) 0.3065(3) 0.46523(14) 0.0477(5) Uani 1 1 d . . . . .
C5 C 0.03787(10) 0.3939(3) 0.41798(14) 0.0491(5) 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
O1 C11 1.421(2) 7_556 ?
O1 C6 1.426(2) . ?
O2 C8 1.414(3) . ?
O2 C7 1.421(2) . ?
O3 C10 1.415(3) . ?
O3 C9 1.421(3) . ?
C6 C7 1.493(3) . ?
C8 C9 1.491(3) . ?
C10 C11 1.489(3) . ?
C11 O1 1.421(2) 7_556 ?
Cl1 C3 1.714(2) . ?
N1 C5 1.305(3) . ?
N1 C1 1.338(3) . ?
C1 N2 1.354(3) . ?
C1 C2 1.399(3) . ?
F1 C2 1.342(2) . ?
C2 C3 1.378(3) . ?
F2 C4 1.350(2) . ?
C3 C4 1.373(3) . ?
F3 C5 1.341(3) . ?
C4 C5 1.369(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
C11 O1 C6 112.37(15) 7_556 . ?
C8 O2 C7 110.96(16) . . ?
C10 O3 C9 112.33(16) . . ?
O1 C6 C7 109.43(16) . . ?
O2 C7 C6 110.10(16) . . ?
O2 C8 C9 109.96(17) . . ?
O3 C9 C8 109.73(18) . . ?
O3 C10 C11 109.26(17) . . ?
O1 C11 C10 109.50(16) 7_556 . ?
C5 N1 C1 119.11(18) . . ?
N1 C1 N2 119.32(19) . . ?
N1 C1 C2 119.05(17) . . ?
N2 C1 C2 121.58(19) . . ?
F1 C2 C3 120.02(18) . . ?
F1 C2 C1 119.02(17) . . ?
C3 C2 C1 120.95(18) . . ?
C4 C3 C2 118.13(18) . . ?
C4 C3 Cl1 120.74(16) . . ?
C2 C3 Cl1 121.12(16) . . ?
F2 C4 C5 121.3(2) . . ?
F2 C4 C3 121.2(2) . . ?
C5 C4 C3 117.45(18) . . ?
N1 C5 F3 116.7(2) . . ?
N1 C5 C4 125.2(2) . . ?
F3 C5 C4 118.08(19) . . ?

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_2Bxcr-m202
_database_code_depnum_ccdc_archive 'CCDC 1911499'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
4-amino-3-chloro-2,5,6-trifluoropyridine 18-crown-6, associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          394
_chemical_formula_moiety         '2(C5 H2 Cl F3 N2), C12 H24 O6'
_chemical_formula_sum            'C22 H28 Cl2 F6 N4 O6'
_chemical_formula_weight         629.38

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      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                   19.1536(10)
_cell_length_b                   9.5830(5)
_cell_length_c                   17.3666(14)
_cell_angle_alpha                90
_cell_angle_beta                 118.714(2)
_cell_angle_gamma                90
_cell_volume                     2795.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.316
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7631
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22277
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.425
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3208
_reflns_number_gt                2549
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0662P)²+3.0604P] 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         3208
_refine_ls_number_parameters     198
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1389
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.080
_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
O1 O 0.48628(11) 0.19855(19) 0.35556(12) 0.0689(5) Uani 1 1 d . . . A 1
O2 O 0.58108(9) 0.21175(16) 0.53806(10) 0.0542(4) Uani 1 1 d . . . A 1
O3 O 0.62244(9) 0.03852(19) 0.68380(11) 0.0597(4) Uani 1 1 d D . . A 1
C6 C 0.48040(18) 0.3088(3) 0.4047(2) 0.0756(8) Uani 1 1 d . . . A 1
H6A H 0.4411 0.2869 0.4229 0.091 Uiso 1 1 calc R U . A 1
H6B H 0.4635 0.3927 0.3691 0.091 Uiso 1 1 calc R U . A 1
C7 C 0.55924(17) 0.3322(2) 0.48315(19) 0.0668(7) Uani 1 1 d . . . A 1
H7A H 0.5990 0.3503 0.4649 0.080 Uiso 1 1 calc R U . A 1
H7B H 0.5566 0.4129 0.5154 0.080 Uiso 1 1 calc R U . A 1
C8 C 0.65009(15) 0.2341(3) 0.61952(16) 0.0641(7) Uani 1 1 d . . . A 1
H8A H 0.6378 0.2957 0.6557 0.077 Uiso 1 1 calc R U . A 1
H8B H 0.6909 0.2781 0.6100 0.077 Uiso 1 1 calc R U . A 1
C9 C 0.67934(13) 0.0994(3) 0.66452(16) 0.0623(7) Uani 1 1 d . . . A 1
H9A H 0.6900 0.0370 0.6274 0.075 Uiso 1 1 calc R U . A 1
H9B H 0.7288 0.1137 0.7185 0.075 Uiso 1 1 calc R U . A 1
C10 C 0.64759(17) -0.0988(3) 0.7169(2) 0.0570(10) Uani 0.807(9) 1 d . . P A 1
H10A H 0.6958 -0.0946 0.7732 0.068 Uiso 1 1 calc R U . A 1
H10B H 0.6589 -0.1518 0.6766 0.068 Uiso 1 1 calc R U . A 1
C11 C 0.58328(19) -0.1676(4) 0.72720(19) 0.0594(11) Uani 0.807(9) 1 d . . P A 1
H11A H 0.6036 -0.2538 0.7597 0.071 Uiso 1 1 calc R U . A 1
H11B H 0.5679 -0.1074 0.7614 0.071 Uiso 1 1 calc R U . A 1
C10A C 0.6184(12) -0.0670(16) 0.7384(10) 0.080(6) Uiso 0.193(9) 1 d D . P A 2
C11A C 0.6043(8) -0.2032(17) 0.6916(12) 0.080(6) Uiso 0.193(9) 1 d D . P A 2
Cl1 Cl 0.28866(4) -0.07428(7) 0.53189(5) 0.0678(2) Uani 1 1 d . . . . .
F1 F 0.20649(10) 0.1111(2) 0.59338(13) 0.0886(6) Uani 1 1 d . . . . .
C1 C 0.27509(14) 0.1654(3) 0.60303(15) 0.0581(6) Uani 1 1 d . . . . .
N1 N 0.29278(15) 0.2895(3) 0.63793(14) 0.0693(6) Uani 1 1 d . . . . .
C2 C 0.31928(12) 0.0874(2) 0.57589(13) 0.0452(5) Uani 1 1 d . . . . .
N2 N 0.43708(12) 0.0771(2) 0.55863(17) 0.0623(6) Uani 1 1 d D . . . .
H2A H 0.4828(12) 0.113(3) 0.5730(19) 0.075(9) Uiso 1 1 d D . . . .
H2B H 0.4300(16) -0.0082(19) 0.5461(17) 0.063(7) Uiso 1 1 d D . . . .
F2 F 0.47865(10) 0.33980(17) 0.63584(14) 0.0860(5) Uani 1 1 d . . . . .
C3 C 0.39099(12) 0.1419(2) 0.58550(13) 0.0440(4) Uani 1 1 d . . . . .
F3 F 0.37946(15) 0.4687(2) 0.68278(15) 0.1115(7) Uani 1 1 d . . . . .
C4 C 0.40923(15) 0.2757(2) 0.62293(16) 0.0584(6) Uani 1 1 d . . . . .
C5 C 0.35967(19) 0.3406(3) 0.64717(17) 0.0686(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
O1 C6 1.396(4) . ?
O1 C11 1.445(3) 5_656 ?
O2 C8 1.413(3) . ?
O2 C7 1.426(3) . ?
O3 C9 1.411(3) . ?
O3 C10 1.425(3) . ?
C6 C7 1.487(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.473(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.481(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O1 1.445(3) 5_656 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10A C11A 1.491(17) . ?
Cl1 C2 1.702(2) . ?
F1 C1 1.347(3) . ?
C1 N1 1.304(4) . ?
C1 C2 1.371(3) . ?
N1 C5 1.308(4) . ?
C2 C3 1.403(3) . ?
N2 C3 1.334(3) . ?
N2 H2A 0.859(17) . ?
N2 H2B 0.840(17) . ?
F2 C4 1.382(3) . ?
C3 C4 1.403(3) . ?
F3 C5 1.345(3) . ?
C4 C5 1.360(4) . ?

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 O1 C11 117.2(2) . 5_656 ?
C8 O2 C7 112.30(19) . . ?
C9 O3 C10 109.2(2) . . ?
O1 C6 C7 109.3(2) . . ?
O1 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
O1 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
O2 C7 C6 109.5(2) . . ?
O2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
O2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
O2 C8 C9 109.4(2) . . ?
O2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
O2 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O3 C9 C8 110.4(2) . . ?
O3 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
O3 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O3 C10 C11 108.7(3) . . ?
O3 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
O3 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
O1 C11 C10 113.2(2) 5_656 . ?
O1 C11 H11A 108.9 5_656 . ?
C10 C11 H11A 108.9 . . ?
O1 C11 H11B 108.9 5_656 . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N1 C1 F1 115.5(2) . . ?
N1 C1 C2 126.3(2) . . ?
F1 C1 C2 118.2(2) . . ?
C1 N1 C5 114.8(2) . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 Cl1 120.91(18) . . ?
C3 C2 Cl1 119.95(15) . . ?
C3 N2 H2A 118(2) . . ?
C3 N2 H2B 119.5(19) . . ?
H2A N2 H2B 119(3) . . ?
N2 C3 C4 121.9(2) . . ?
N2 C3 C2 124.02(19) . . ?
C4 C3 C2 114.04(19) . . ?
C5 C4 F2 120.5(2) . . ?
C5 C4 C3 120.4(2) . . ?
F2 C4 C3 119.2(2) . . ?
N1 C5 F3 116.2(3) . . ?
N1 C5 C4 125.4(2) . . ?
F3 C5 C4 118.4(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
C11 O1 C6 C7 -175.2(2) 5_656 . . . ?
C8 O2 C7 C6 -171.9(2) . . . . ?
O1 C6 C7 O2 -63.5(3) . . . . ?
C7 O2 C8 C9 -167.7(2) . . . . ?
C10 O3 C9 C8 172.6(2) . . . . ?
O2 C8 C9 O3 -63.2(3) . . . . ?
C9 O3 C10 C11 -173.5(2) . . . . ?
O3 C10 C11 O1 69.2(3) . . . 5_656 ?
F1 C1 N1 C5 179.8(2) . . . . ?
C2 C1 N1 C5 -0.3(4) . . . . ?
N1 C1 C2 C3 0.2(4) . . . . ?
F1 C1 C2 C3 -179.9(2) . . . . ?
N1 C1 C2 Cl1 179.62(19) . . . . ?
F1 C1 C2 Cl1 -0.5(3) . . . . ?
C1 C2 C3 N2 -177.6(2) . . . . ?
Cl1 C2 C3 N2 2.9(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
Cl1 C2 C3 C4 -179.75(16) . . . . ?
N2 C3 C4 C5 178.0(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
N2 C3 C4 F2 -2.8(4) . . . . ?
C2 C3 C4 F2 179.8(2) . . . . ?
C1 N1 C5 F3 179.8(2) . . . . ?
C1 N1 C5 C4 0.6(4) . . . . ?
F2 C4 C5 N1 180.0(3) . . . . ?
C3 C4 C5 N1 -0.8(4) . . . . ?
F2 C4 C5 F3 0.8(4) . . . . ?
C3 C4 C5 F3 180.0(2) . . . . ?

_refine_diff_density_max         0.521
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_2Dxcr-M19_2
_database_code_depnum_ccdc_archive 'CCDC 1911501'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2-amino-3,5,6-trifluoropyridine 18-crown-6, associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          373
_chemical_formula_moiety         '2(C5 H3 F3 N2), C12 H24 O6'
_chemical_formula_sum            'C22 H30 F6 N4 O6'
_chemical_formula_weight         560.50

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           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                   8.722(2)
_cell_length_b                   16.464(4)
_cell_length_c                   9.500(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.139(9)
_cell_angle_gamma                90
_cell_volume                     1343.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4630
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      22.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9014
_exptl_absorpt_correction_T_max  0.9512
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18817
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.372
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2649
_reflns_number_gt                1664
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0786P)²+0.3682P] 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         2649
_refine_ls_number_parameters     180
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1626
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 1.0279(2) 0.21005(10) 0.3375(2) 0.1070(6) Uani 1 1 d . . . . .
N1 N 0.6835(2) 0.09447(12) 0.22656(19) 0.0641(5) Uani 1 1 d . . . . .
C1 C 0.8169(2) 0.11938(12) 0.3041(2) 0.0535(5) Uani 1 1 d . . . . .
F2 F 0.6326(2) 0.23233(11) -0.07071(16) 0.1033(6) Uani 1 1 d . . . . .
N2 N 0.8698(3) 0.08292(13) 0.4313(2) 0.0710(6) Uani 1 1 d D . . . .
H2N H 0.967(2) 0.0882(19) 0.469(3) 0.099(10) Uiso 1 1 d D . . . .
H1N H 0.824(3) 0.0375(13) 0.448(3) 0.085(8) Uiso 1 1 d D . . . .
C2 C 0.8940(3) 0.18452(13) 0.2544(3) 0.0622(6) Uani 1 1 d . . . . .
F3 F 0.4929(2) 0.10526(15) 0.0353(2) 0.1358(9) Uani 1 1 d . . . . .
C3 C 0.8369(3) 0.22388(13) 0.1299(2) 0.0659(6) Uani 1 1 d . . . . .
H3A H 0.8900 0.2672 0.0979 0.079 Uiso 1 1 calc R U . . .
C4 C 0.6984(3) 0.19688(15) 0.0543(2) 0.0655(6) Uani 1 1 d . . . . .
C5 C 0.6289(3) 0.13317(16) 0.1079(2) 0.0710(7) Uani 1 1 d . . . . .
O1 O 0.8696(2) 0.00283(11) 0.7531(2) 0.0878(6) Uani 1 1 d . . . . .
O2 O 0.7143(2) -0.07604(11) 0.5049(2) 0.0884(6) Uani 1 1 d . . . . .
O3 O 0.8795(2) -0.11317(10) 0.28510(17) 0.0778(5) Uani 1 1 d . . . . .
C6 C 0.7054(4) -0.0071(2) 0.7205(4) 0.1119(12) Uani 1 1 d . . . . .
H6A H 0.6590 0.0385 0.6637 0.134 Uiso 1 1 calc R U . . .
H6B H 0.6630 -0.0086 0.8083 0.134 Uiso 1 1 calc R U . . .
C7 C 0.6677(4) -0.0837(2) 0.6399(4) 0.1100(11) Uani 1 1 d . . . . .
H7A H 0.7220 -0.1288 0.6924 0.132 Uiso 1 1 calc R U . . .
H7B H 0.5567 -0.0942 0.6272 0.132 Uiso 1 1 calc R U . . .
C8 C 0.6811(3) -0.14601(19) 0.4175(4) 0.0966(9) Uani 1 1 d . . . . .
H8A H 0.5721 -0.1606 0.4097 0.116 Uiso 1 1 calc R U . . .
H8B H 0.7437 -0.1914 0.4597 0.116 Uiso 1 1 calc R U . . .
C9 C 0.7166(4) -0.12799(18) 0.2747(3) 0.0966(10) Uani 1 1 d . . . . .
H9A H 0.6860 -0.1735 0.2112 0.116 Uiso 1 1 calc R U . . .
H9B H 0.6583 -0.0806 0.2352 0.116 Uiso 1 1 calc R U . . .
C10 C 0.9162(5) -0.08828(18) 0.1531(3) 0.0965(10) Uani 1 1 d . . . . .
H10A H 0.8606 -0.0386 0.1221 0.116 Uiso 1 1 calc R U . . .
H10B H 0.8836 -0.1297 0.0815 0.116 Uiso 1 1 calc R U . . .
C11 C 1.0853(5) -0.07445(17) 0.1669(3) 0.1002(11) Uani 1 1 d . . . . .
H11A H 1.1412 -0.1206 0.2142 0.120 Uiso 1 1 calc R U . . .
H11B H 1.1125 -0.0694 0.0726 0.120 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.356(3) . ?
N1 C5 1.309(3) . ?
N1 C1 1.328(3) . ?
C1 N2 1.355(3) . ?
C1 C2 1.391(3) . ?
F2 C4 1.357(3) . ?
C2 C3 1.364(3) . ?
F3 C5 1.344(3) . ?
C3 C4 1.367(3) . ?
C4 C5 1.355(3) . ?
O1 C11 1.421(4) 3_756 ?
O1 C6 1.420(4) . ?
O2 C8 1.420(4) . ?
O2 C7 1.417(4) . ?
O3 C10 1.408(3) . ?
O3 C9 1.428(4) . ?
C6 C7 1.483(5) . ?
C8 C9 1.474(4) . ?
C10 C11 1.476(5) . ?
C11 O1 1.420(4) 3_756 ?

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
C5 N1 C1 118.54(19) . . ?
N1 C1 N2 119.0(2) . . ?
N1 C1 C2 118.60(19) . . ?
N2 C1 C2 122.3(2) . . ?
C3 C2 F1 120.2(2) . . ?
C3 C2 C1 122.4(2) . . ?
F1 C2 C1 117.4(2) . . ?
C2 C3 C4 117.1(2) . . ?
C5 C4 F2 120.9(2) . . ?
C5 C4 C3 117.8(2) . . ?
F2 C4 C3 121.2(2) . . ?
N1 C5 C4 125.5(2) . . ?
N1 C5 F3 115.5(2) . . ?
C4 C5 F3 119.0(2) . . ?
C11 O1 C6 112.7(2) 3_756 . ?
C8 O2 C7 113.3(2) . . ?
C10 O3 C9 111.6(2) . . ?
O1 C6 C7 109.5(2) . . ?
O2 C7 C6 108.6(2) . . ?
O2 C8 C9 108.7(2) . . ?
O3 C9 C8 109.8(2) . . ?
O3 C10 C11 110.2(2) . . ?
O1 C11 C10 110.7(2) 3_756 . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_2Gxcr-M15_1
_database_code_depnum_ccdc_archive 'CCDC 1911504'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
7-amino-2-chloro-5,6,8-trifluoroquinoline 18-crown-6, associate 2:1
;
_chemical_name_common            ?
_chemical_melting_point          415
_chemical_formula_moiety         '2(C9 H4 Cl F3 N2), C12 H24 O6'
_chemical_formula_sum            'C30 H32 Cl2 F6 N4 O6'
_chemical_formula_weight         729.49

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.5421(5)
_cell_length_b                   9.4386(3)
_cell_length_c                   14.5435(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.472(2)
_cell_angle_gamma                90
_cell_volume                     1651.00(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      29.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.279
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7995
_exptl_absorpt_correction_T_max  0.8374
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36550
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0423
_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       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.530
_diffrn_reflns_theta_max         30.140
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4872
_reflns_number_gt                3681
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0899P)²+0.8013P] 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         4872
_refine_ls_number_parameters     225
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_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 0.73146(4) 0.42712(7) 0.23444(4) 0.06643(19) Uani 1 1 d . . . . .
F1 F 0.40810(13) 0.89452(15) -0.06333(12) 0.0816(4) Uani 1 1 d . . . . .
O1 O -0.07919(14) 0.54506(19) -0.19613(11) 0.0676(4) Uani 1 1 d . . . . .
N1 N 0.52862(11) 0.50322(15) 0.15258(10) 0.0425(3) Uani 1 1 d . . . . .
C1 C 0.63132(13) 0.53576(19) 0.15937(11) 0.0433(3) Uani 1 1 d . . . . .
F2 F 0.19522(11) 0.82780(15) -0.07678(11) 0.0715(4) Uani 1 1 d . . . . .
O2 O -0.06730(13) 0.77974(19) -0.07137(13) 0.0712(4) Uani 1 1 d . . . . .
N2 N 0.14080(14) 0.6037(2) 0.02127(17) 0.0691(5) Uani 1 1 d D . . . .
H2A H 0.0937(19) 0.656(3) -0.0156(16) 0.077(8) Uiso 1 1 d D . . . .
H2B H 0.130(2) 0.539(2) 0.0578(17) 0.083(9) Uiso 1 1 d D . . . .
C2 C 0.66788(15) 0.6475(2) 0.11247(14) 0.0508(4) Uani 1 1 d . . . . .
H2 H 0.7431 0.6634 0.1203 0.061 Uiso 1 1 calc R U . . .
F3 F 0.31207(10) 0.44424(14) 0.13253(11) 0.0711(4) Uani 1 1 d . . . . .
O3 O -0.04613(13) 0.70872(17) 0.12425(12) 0.0656(4) Uani 1 1 d . . . . .
C3 C 0.58839(16) 0.7318(2) 0.05495(15) 0.0520(4) Uani 1 1 d . . . . .
H3 H 0.6089 0.8079 0.0231 0.062 Uiso 1 1 calc R U . . .
C3A C 0.47494(13) 0.70376(17) 0.04372(11) 0.0405(3) Uani 1 1 d . . . . .
C4 C 0.38609(16) 0.78301(18) -0.01364(14) 0.0489(4) Uani 1 1 d . . . . .
C5 C 0.27847(15) 0.74981(19) -0.02073(13) 0.0480(4) Uani 1 1 d . . . . .
C6 C 0.24850(13) 0.63405(19) 0.02856(12) 0.0445(3) Uani 1 1 d . . . . .
C7A C 0.44821(12) 0.58639(15) 0.09401(10) 0.0361(3) Uani 1 1 d . . . . .
C7 C 0.33648(13) 0.55634(17) 0.08452(12) 0.0428(3) Uani 1 1 d . . . . .
C8 C -0.0748(2) 0.6862(3) -0.22477(18) 0.0818(8) Uani 1 1 d . . . . .
H8A H -0.1124 0.6952 -0.2927 0.098 Uiso 1 1 calc R U . . .
H8B H 0.0021 0.7145 -0.2143 0.098 Uiso 1 1 calc R U . . .
C9 C -0.1284(2) 0.7795(3) -0.1697(2) 0.0781(7) Uani 1 1 d . . . . .
H9A H -0.1325 0.8752 -0.1948 0.094 Uiso 1 1 calc R U . . .
H9B H -0.2035 0.7469 -0.1765 0.094 Uiso 1 1 calc R U . . .
C10 C -0.1218(2) 0.8496(3) -0.0134(2) 0.0798(8) Uani 1 1 d . . . . .
H10A H -0.1920 0.8030 -0.0178 0.096 Uiso 1 1 calc R U . . .
H10B H -0.1373 0.9466 -0.0350 0.096 Uiso 1 1 calc R U . . .
C11 C -0.0511(3) 0.8481(3) 0.0875(2) 0.0814(8) Uani 1 1 d . . . . .
H11A H 0.0231 0.8807 0.0905 0.098 Uiso 1 1 calc R U . . .
H11B H -0.0820 0.9115 0.1258 0.098 Uiso 1 1 calc R U . . .
C12 C 0.0324(2) 0.6966(3) 0.2153(2) 0.0816(8) Uani 1 1 d . . . . .
H12A H 0.0133 0.7613 0.2600 0.098 Uiso 1 1 calc R U . . .
H12B H 0.1057 0.7216 0.2108 0.098 Uiso 1 1 calc R U . . .
C13 C 0.0333(2) 0.5488(4) 0.25065(17) 0.0812(8) Uani 1 1 d . . . . .
H13A H 0.0766 0.5444 0.3174 0.097 Uiso 1 1 calc R U . . .
H13B H -0.0421 0.5197 0.2465 0.097 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 C1 1.7445(18) . ?
F1 C4 1.349(2) . ?
O1 C8 1.402(3) . ?
O1 C13 1.416(3) 3_565 ?
N1 C1 1.300(2) . ?
N1 C7A 1.368(2) . ?
C1 C2 1.402(3) . ?
F2 C5 1.347(2) . ?
O2 C10 1.393(3) . ?
O2 C9 1.418(3) . ?
N2 C6 1.355(2) . ?
N2 H2A 0.837(10) . ?
N2 H2B 0.842(10) . ?
C2 C3 1.362(3) . ?
C2 H2 0.9300 . ?
F3 C7 1.3498(19) . ?
O3 C12 1.414(3) . ?
O3 C11 1.415(3) . ?
C3 C3A 1.411(2) . ?
C3 H3 0.9300 . ?
C3A C4 1.404(2) . ?
C3A C7A 1.419(2) . ?
C4 C5 1.361(3) . ?
C5 C6 1.415(3) . ?
C6 C7 1.382(2) . ?
C7A C7 1.398(2) . ?
C8 C9 1.475(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.483(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.486(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O1 1.416(3) 3_565 ?
C13 H13A 0.9700 . ?
C13 H13B 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
C8 O1 C13 111.8(2) . 3_565 ?
C1 N1 C7A 116.82(14) . . ?
N1 C1 C2 126.46(16) . . ?
N1 C1 Cl1 115.50(13) . . ?
C2 C1 Cl1 118.04(13) . . ?
C10 O2 C9 113.2(2) . . ?
C6 N2 H2A 116(2) . . ?
C6 N2 H2B 116(2) . . ?
H2A N2 H2B 128(3) . . ?
C3 C2 C1 117.07(16) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C12 O3 C11 111.9(2) . . ?
C2 C3 C3A 120.02(16) . . ?
C2 C3 H3 120.0 . . ?
C3A C3 H3 120.0 . . ?
C4 C3A C3 125.00(16) . . ?
C4 C3A C7A 117.30(15) . . ?
C3 C3A C7A 117.70(15) . . ?
F1 C4 C5 119.24(17) . . ?
F1 C4 C3A 119.06(17) . . ?
C5 C4 C3A 121.71(15) . . ?
F2 C5 C4 120.13(16) . . ?
F2 C5 C6 117.20(16) . . ?
C4 C5 C6 122.67(16) . . ?
N2 C6 C7 123.07(17) . . ?
N2 C6 C5 121.72(17) . . ?
C7 C6 C5 115.21(15) . . ?
N1 C7A C7 119.11(14) . . ?
N1 C7A C3A 121.92(14) . . ?
C7 C7A C3A 118.97(14) . . ?
F3 C7 C6 117.42(14) . . ?
F3 C7 C7A 118.43(14) . . ?
C6 C7 C7A 124.15(15) . . ?
O1 C8 C9 110.1(2) . . ?
O1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
O1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
O2 C9 C8 110.5(2) . . ?
O2 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
O2 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O2 C10 C11 109.7(2) . . ?
O2 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
O2 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O3 C11 C10 109.4(2) . . ?
O3 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
O3 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
O3 C12 C13 109.5(2) . . ?
O3 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
O3 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
O1 C13 C12 111.0(2) 3_565 . ?
O1 C13 H13A 109.4 3_565 . ?
C12 C13 H13A 109.4 . . ?
O1 C13 H13B 109.4 3_565 . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?

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
C7A N1 C1 C2 -0.1(3) . . . . ?
C7A N1 C1 Cl1 -179.85(11) . . . . ?
N1 C1 C2 C3 0.9(3) . . . . ?
Cl1 C1 C2 C3 -179.38(14) . . . . ?
C1 C2 C3 C3A -0.8(3) . . . . ?
C2 C3 C3A C4 -179.87(18) . . . . ?
C2 C3 C3A C7A 0.0(3) . . . . ?
C3 C3A C4 F1 0.6(3) . . . . ?
C7A C3A C4 F1 -179.34(16) . . . . ?
C3 C3A C4 C5 -179.76(18) . . . . ?
C7A C3A C4 C5 0.3(3) . . . . ?
F1 C4 C5 F2 0.0(3) . . . . ?
C3A C4 C5 F2 -179.71(17) . . . . ?
F1 C4 C5 C6 179.58(18) . . . . ?
C3A C4 C5 C6 -0.1(3) . . . . ?
F2 C5 C6 N2 -1.1(3) . . . . ?
C4 C5 C6 N2 179.3(2) . . . . ?
F2 C5 C6 C7 179.46(16) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C1 N1 C7A C7 -179.72(15) . . . . ?
C1 N1 C7A C3A -0.7(2) . . . . ?
C4 C3A C7A N1 -179.32(15) . . . . ?
C3 C3A C7A N1 0.8(2) . . . . ?
C4 C3A C7A C7 -0.3(2) . . . . ?
C3 C3A C7A C7 179.77(16) . . . . ?
N2 C6 C7 F3 0.9(3) . . . . ?
C5 C6 C7 F3 -179.61(16) . . . . ?
N2 C6 C7 C7A -179.30(19) . . . . ?
C5 C6 C7 C7A 0.2(3) . . . . ?
N1 C7A C7 F3 -1.1(2) . . . . ?
C3A C7A C7 F3 179.85(15) . . . . ?
N1 C7A C7 C6 179.09(16) . . . . ?
C3A C7A C7 C6 0.1(3) . . . . ?
C13 O1 C8 C9 177.2(2) 3_565 . . . ?
C10 O2 C9 C8 -171.4(2) . . . . ?
O1 C8 C9 O2 65.6(3) . . . . ?
C9 O2 C10 C11 -178.5(2) . . . . ?
C12 O3 C11 C10 171.6(2) . . . . ?
O2 C10 C11 O3 -70.3(3) . . . . ?
C11 O3 C12 C13 179.5(2) . . . . ?
O3 C12 C13 O1 69.5(3) . . . 3_565 ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.050

