# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_t705_pl-A15cr5
_database_code_depnum_ccdc_archive 'CCDC 2362725'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2024-06-14 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
2,4,5-trifluoro-1,3-phenylenediamine 15-crown-5, associate 1:1
;
_chemical_name_common            ?
_chemical_melting_point          350
_chemical_formula_moiety         'C6 H5 N2 F3, C10 H20 O5'
_chemical_formula_sum            'C16 H25 F3 N2 O5'
_chemical_formula_weight         382.38

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   24.457(5)
_cell_length_b                   8.6861(17)
_cell_length_c                   18.097(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.435(9)
_cell_angle_gamma                90
_cell_volume                     3844.3(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4449
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.73

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8154
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   SADABS-2016/2
_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            13107
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.665
_diffrn_reflns_theta_max         25.087
_diffrn_reflns_theta_full        25.087
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3382
_reflns_number_gt                2440
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1285P)²+6.6866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3382
_refine_ls_number_parameters     262
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0954
_refine_ls_wR_factor_ref         0.2499
_refine_ls_wR_factor_gt          0.2285
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.070
_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 -0.17313(12) -0.0276(3) 0.37172(19) 0.0611(9) Uani 1 1 d . . . . .
F3 F -0.05066(19) 0.4874(5) 0.3641(4) 0.1243(19) Uani 1 1 d . . . . .
F2A F -0.0840(4) 0.4024(10) 0.4805(5) 0.106(3) Uani 0.5 1 d . . P . .
F2 F -0.0678(3) 0.3435(7) 0.2467(4) 0.0647(18) Uani 0.5 1 d . . P . .
N1 N -0.1563(2) 0.1325(7) 0.4991(2) 0.0711(15) Uani 1 1 d . . . . .
H1A H -0.150671 0.189557 0.537162 0.085 Uiso 1 1 d R U . . .
H1B H -0.175911 0.050307 0.503062 0.085 Uiso 1 1 d R U . . .
N2 N -0.1326(3) 0.0658(7) 0.2398(3) 0.0889(19) Uani 1 1 d . . . . .
H2A H -0.153931 -0.012693 0.240431 0.107 Uiso 1 1 d R U . . .
H2B H -0.117851 0.094717 0.199091 0.107 Uiso 1 1 d R U . . .
C1 C -0.13317(19) 0.1789(5) 0.4357(3) 0.0387(11) Uani 1 1 d . . . . .
C2 C -0.14185(16) 0.1009(4) 0.3701(2) 0.0322(10) Uani 1 1 d . . . . .
C3 C -0.12244(19) 0.1470(5) 0.3027(3) 0.0393(11) Uani 1 1 d . . . . .
C4 C -0.0910(2) 0.2797(6) 0.3028(3) 0.0522(14) Uani 1 1 d . . . . .
H4 H -0.075610 0.316580 0.257000 0.063 Uiso 0.5 1 d . U P . .
C5 C -0.0815(2) 0.3572(6) 0.3658(4) 0.0636(16) Uani 1 1 d . . . . .
C6 C -0.1011(2) 0.3116(6) 0.4317(4) 0.0573(16) Uani 1 1 d . . . . .
H6 H -0.093011 0.369921 0.475929 0.069 Uiso 0.5 1 d . U P . .
O1 O -0.21410(18) 0.1380(5) 0.6659(2) 0.0702(12) Uani 1 1 d . . . . .
O2A O -0.11425(19) 0.3007(6) 0.6416(3) 0.0885(15) Uani 0.5 1 d D U P . .
O3A O -0.0432(2) 0.0864(7) 0.5872(3) 0.1007(17) Uani 0.5 1 d D . P . .
O4 O -0.10399(18) -0.1958(6) 0.5926(2) 0.0756(13) Uani 1 1 d . . . . .
O5 O -0.21485(18) -0.1286(5) 0.5767(3) 0.0713(12) Uani 1 1 d . . . . .
C7 C -0.2100(3) 0.2982(8) 0.6635(4) 0.0746(19) Uani 1 1 d . . . A 1
H7A H -0.238087 0.344517 0.693770 0.090 Uiso 1 1 calc R U . A 1
H7B H -0.214600 0.334411 0.613177 0.090 Uiso 1 1 calc R U . A 1
C8A C -0.1539(3) 0.3419(8) 0.6926(4) 0.079(2) Uani 0.5 1 d D . P A 1
H8A H -0.152421 0.451973 0.701373 0.095 Uiso 1 1 calc R U . A 1
H8B H -0.146939 0.289725 0.739111 0.095 Uiso 1 1 calc R U . A 1
C9A C -0.0631(4) 0.2660(17) 0.6791(7) 0.058(4) Uani 0.58(2) 1 d D U P A 1
H9A1 H -0.067930 0.182462 0.714054 0.070 Uiso 0.58(2) 1 calc R U P A 1
H9A2 H -0.049729 0.355627 0.705684 0.070 Uiso 0.58(2) 1 calc R U P A 1
C10A C -0.0236(6) 0.2203(14) 0.6199(8) 0.075(5) Uani 0.58(2) 1 d D U P A 1
H10A H -0.020760 0.301562 0.583396 0.090 Uiso 0.58(2) 1 calc R U P A 1
H10B H 0.012351 0.202537 0.641225 0.090 Uiso 0.58(2) 1 calc R U P A 1
C11A C -0.0209(3) -0.0552(8) 0.6033(5) 0.084(2) Uani 0.5 1 d D . P A 1
H11A H -0.022668 -0.074017 0.656083 0.101 Uiso 1 1 calc R U . A 1
H11B H 0.017125 -0.057348 0.588730 0.101 Uiso 1 1 calc R U . A 1
C12 C -0.0522(3) -0.1772(9) 0.5626(5) 0.092(2) Uani 1 1 d . . . A 1
H12A H -0.055606 -0.148781 0.510896 0.110 Uiso 1 1 calc R U . A 1
H12B H -0.032433 -0.273864 0.565395 0.110 Uiso 1 1 calc R U . A 1
C13 C -0.1398(3) -0.2881(8) 0.5508(4) 0.081(2) Uani 1 1 d . . . B 1
H13A H -0.127221 -0.393986 0.551389 0.097 Uiso 1 1 calc R U . B 1
H13B H -0.140707 -0.252837 0.499988 0.097 Uiso 1 1 calc R U . B 1
C14 C -0.1957(3) -0.2784(7) 0.5833(5) 0.083(2) Uani 1 1 d . . . B 1
H14A H -0.220191 -0.348356 0.557484 0.100 Uiso 1 1 calc R U . B 1
H14B H -0.194382 -0.308001 0.634926 0.100 Uiso 1 1 calc R U . B 1
C15 C -0.2574(2) -0.0893(9) 0.6236(4) 0.0738(18) Uani 1 1 d . . . C 1
H15A H -0.250853 -0.132969 0.672146 0.089 Uiso 1 1 calc R U . C 1
H15B H -0.291517 -0.130754 0.604491 0.089 Uiso 1 1 calc R U . C 1
C16 C -0.2614(2) 0.0814(8) 0.6292(4) 0.0734(17) Uani 1 1 d . . . C 1
H16A H -0.264160 0.126147 0.580215 0.088 Uiso 1 1 calc R U . C 1
H16B H -0.293812 0.109560 0.656603 0.088 Uiso 1 1 calc R U . C 1
O2B O -0.11425(19) 0.3007(6) 0.6416(3) 0.0885(15) Uani 0.5 1 d D . P A 2
O3B O -0.0432(2) 0.0864(7) 0.5872(3) 0.1007(17) Uani 0.5 1 d D U P A 2
C8B C -0.1539(3) 0.3419(8) 0.6926(4) 0.079(2) Uani 0.5 1 d D . P A 2
C9B C -0.0586(6) 0.326(2) 0.6510(19) 0.108(10) Uani 0.42(2) 1 d D U P A 2
H9BA H -0.050000 0.394529 0.687610 0.130 Uiso 0.42(2) 1 d . U P A 2
H9BB H -0.045931 0.381021 0.601801 0.130 Uiso 0.42(2) 1 d . U P A 2
C10B C -0.0299(10) 0.173660 0.654040 0.122(12) Uani 0.42(2) 1 d D U P A 2
H10C H 0.007030 0.184800 0.660721 0.146 Uiso 0.42(2) 1 d . U P A 2
H10D H -0.046200 0.121271 0.696321 0.146 Uiso 0.42(2) 1 d . U P A 2
C11B C -0.0209(3) -0.0552(8) 0.6033(5) 0.084(2) Uani 0.5 1 d D . P A 2


_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 1.353(5) . ?
F3 C5 1.360(6) . ?
F2A C6 1.254(9) . ?
F2A H6 0.368(9) . ?
F2 C4 1.292(8) . ?
F2 H4 0.356(5) . ?
N1 C1 1.345(7) . ?
N1 H1A 0.8588 . ?
N1 H1B 0.8627 . ?
N2 C3 1.361(7) . ?
N2 H2A 0.8587 . ?
N2 H2B 0.8599 . ?
C1 C2 1.382(6) . ?
C1 C6 1.396(7) . ?
C2 C3 1.372(6) . ?
C3 C4 1.386(7) . ?
C4 C5 1.342(9) . ?
C4 H4 0.968(5) . ?
C5 C6 1.349(9) . ?
C6 H6 0.966(5) . ?
O1 C7 1.395(8) . ?
O1 C16 1.417(8) . ?
O2A C9B 1.388(15) . ?
O2A C8A 1.390(8) . ?
O2A C8B 1.390(8) . ?
O2A C9A 1.452(11) . ?
O3A C11B 1.375(8) . ?
O3A C11A 1.375(8) . ?
O3A C10A 1.389(12) . ?
O3A C10B 1.462(7) . ?
O4 C12 1.391(8) . ?
O4 C13 1.403(8) . ?
O5 C14 1.388(8) . ?
O5 C15 1.390(7) . ?
C7 C8A 1.513(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8A H8A 0.9700 . ?
C8A H8B 0.9700 . ?
C9A C10A 1.500(14) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A C12 1.498(11) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.494(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.489(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C9B C10B 1.499(17) . ?
C9B H9BA 0.91(2) . ?
C9B H9BB 1.06(3) . ?
C10B H10C 0.91(2) . ?
C10B H10D 0.978(11) . ?

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 F2A H6 32.9(11) . . ?
C4 F2 H4 20.8(9) . . ?
C1 N1 H1A 116.4 . . ?
C1 N1 H1B 123.8 . . ?
H1A N1 H1B 119.8 . . ?
C3 N2 H2A 120.5 . . ?
C3 N2 H2B 119.4 . . ?
H2A N2 H2B 120.2 . . ?
N1 C1 C2 121.5(5) . . ?
N1 C1 C6 122.1(5) . . ?
C2 C1 C6 116.3(4) . . ?
F1 C2 C3 117.4(4) . . ?
F1 C2 C1 118.0(4) . . ?
C3 C2 C1 124.6(4) . . ?
N2 C3 C2 122.0(5) . . ?
N2 C3 C4 122.0(5) . . ?
C2 C3 C4 116.0(5) . . ?
F2 C4 C5 112.2(5) . . ?
F2 C4 C3 127.1(6) . . ?
C5 C4 C3 120.7(5) . . ?
F2 C4 H4 7.5(3) . . ?
C5 C4 H4 119.7(5) . . ?
C3 C4 H4 119.6(6) . . ?
C4 C5 C6 122.9(5) . . ?
C4 C5 F3 119.4(6) . . ?
C6 C5 F3 117.7(7) . . ?
F2A C6 C5 108.6(7) . . ?
F2A C6 C1 131.9(7) . . ?
C5 C6 C1 119.4(5) . . ?
F2A C6 H6 11.9(5) . . ?
C5 C6 H6 120.4(6) . . ?
C1 C6 H6 120.2(6) . . ?
C7 O1 C16 113.0(5) . . ?
C9B O2A C8B 124.5(13) . . ?
C8A O2A C9A 110.3(6) . . ?
C11A O3A C10A 121.6(9) . . ?
C11B O3A C10B 101.7(6) . . ?
C12 O4 C13 115.0(6) . . ?
C14 O5 C15 115.6(6) . . ?
O1 C7 C8A 107.8(5) . . ?
O1 C7 H7A 110.1 . . ?
C8A C7 H7A 110.1 . . ?
O1 C7 H7B 110.1 . . ?
C8A C7 H7B 110.1 . . ?
H7A C7 H7B 108.5 . . ?
O2A C8A C7 109.8(5) . . ?
O2A C8A H8A 109.7 . . ?
C7 C8A H8A 109.7 . . ?
O2A C8A H8B 109.7 . . ?
C7 C8A H8B 109.7 . . ?
H8A C8A H8B 108.2 . . ?
O2A C9A C10A 106.1(11) . . ?
O2A C9A H9A1 110.5 . . ?
C10A C9A H9A1 110.5 . . ?
O2A C9A H9A2 110.5 . . ?
C10A C9A H9A2 110.5 . . ?
H9A1 C9A H9A2 108.7 . . ?
O3A C10A C9A 107.7(11) . . ?
O3A C10A H10A 110.2 . . ?
C9A C10A H10A 110.2 . . ?
O3A C10A H10B 110.2 . . ?
C9A C10A H10B 110.2 . . ?
H10A C10A H10B 108.5 . . ?
O3A C11A C12 109.2(6) . . ?
O3A C11A H11A 109.8 . . ?
C12 C11A H11A 109.8 . . ?
O3A C11A H11B 109.8 . . ?
C12 C11A H11B 109.8 . . ?
H11A C11A H11B 108.3 . . ?
O4 C12 C11A 110.6(6) . . ?
O4 C12 H12A 109.5 . . ?
C11A C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
C11A C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O4 C13 C14 109.0(5) . . ?
O4 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
O4 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
O5 C14 C13 109.2(6) . . ?
O5 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
O5 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
O5 C15 C16 109.6(5) . . ?
O5 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
O5 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O1 C16 C15 108.9(5) . . ?
O1 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
O1 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O2A C9B C10B 108.9(17) . . ?
O2A C9B H9BA 114.3(18) . . ?
C10B C9B H9BA 116(2) . . ?
O2A C9B H9BB 105(2) . . ?
C10B C9B H9BB 106.8(17) . . ?
H9BA C9B H9BB 104(2) . . ?
O3A C10B C9B 109.0(13) . . ?
O3A C10B H10C 112.2(12) . . ?
C9B C10B H10C 111.9(10) . . ?
O3A C10B H10D 108.4(11) . . ?
C9B C10B H10D 104(2) . . ?
H10C C10B H10D 110.7(12) . . ?

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
N1 C1 C2 F1 -2.1(6) . . . . ?
C6 C1 C2 F1 -179.4(4) . . . . ?
N1 C1 C2 C3 175.7(4) . . . . ?
C6 C1 C2 C3 -1.6(6) . . . . ?
F1 C2 C3 N2 -1.8(7) . . . . ?
C1 C2 C3 N2 -179.6(5) . . . . ?
F1 C2 C3 C4 179.4(4) . . . . ?
C1 C2 C3 C4 1.6(6) . . . . ?
N2 C3 C4 F2 0.0(9) . . . . ?
C2 C3 C4 F2 178.8(6) . . . . ?
N2 C3 C4 C5 -179.8(5) . . . . ?
C2 C3 C4 C5 -1.0(7) . . . . ?
F2 C4 C5 C6 -179.3(6) . . . . ?
C3 C4 C5 C6 0.5(8) . . . . ?
F2 C4 C5 F3 0.4(8) . . . . ?
C3 C4 C5 F3 -179.8(5) . . . . ?
C4 C5 C6 F2A 177.4(7) . . . . ?
F3 C5 C6 F2A -2.4(8) . . . . ?
C4 C5 C6 C1 -0.5(8) . . . . ?
F3 C5 C6 C1 179.8(5) . . . . ?
N1 C1 C6 F2A 6.4(11) . . . . ?
C2 C1 C6 F2A -176.3(8) . . . . ?
N1 C1 C6 C5 -176.3(5) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
C16 O1 C7 C8A -170.5(5) . . . . ?
C9A O2A C8A C7 -150.6(8) . . . . ?
O1 C7 C8A O2A 71.2(7) . . . . ?
C8A O2A C9A C10A 179.0(9) . . . . ?
C11A O3A C10A C9A -102.9(12) . . . . ?
O2A C9A C10A O3A -63.8(16) . . . . ?
C10A O3A C11A C12 177.3(8) . . . . ?
C13 O4 C12 C11A 169.6(6) . . . . ?
O3A C11A C12 O4 -70.8(8) . . . . ?
C12 O4 C13 C14 -171.5(6) . . . . ?
C15 O5 C14 C13 -160.5(6) . . . . ?
O4 C13 C14 O5 64.2(8) . . . . ?
C14 O5 C15 C16 161.3(6) . . . . ?
C7 O1 C16 C15 170.5(5) . . . . ?
O5 C15 C16 O1 -66.9(7) . . . . ?
C8B O2A C9B C10B 116.5(15) . . . . ?
C11B O3A C10B C9B -171.6(15) . . . . ?
O2A C9B C10B O3A 56(3) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.062


####################################################################### 
# 
# 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_t701_1_2C15cr5
_database_code_depnum_ccdc_archive 'CCDC 2362727'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2024-06-14 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
Co-crystal of 2,4-diaminotrifluoronitrobenzene and 15-crown-5, 2:1
;
_chemical_name_common            ?
_chemical_melting_point          362
_chemical_formula_moiety         '2(C6 H4 F3 N3 O2), C10 H20 O5'
_chemical_formula_sum            'C22 H28 F6 N6 O9'
_chemical_formula_weight         634.50

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      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                   11.5203(14)
_cell_length_b                   11.5359(15)
_cell_length_c                   11.8617(17)
_cell_angle_alpha                106.975(5)
_cell_angle_beta                 108.550(4)
_cell_angle_gamma                90.001(5)
_cell_volume                     1421.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4613
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      25.05

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9149
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   SADABS-2016/2
_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            14729
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.597
_diffrn_reflns_theta_max         25.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5290
_reflns_number_gt                3401
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0899P)²+1.2101P] 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         5290
_refine_ls_number_parameters     398
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.2010
_refine_ls_wR_factor_gt          0.1710
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.050
_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 1.15281(16) 0.18351(19) 0.53490(18) 0.0563(5) Uani 1 1 d . . . . .
N1 N 0.7503(3) 0.0893(2) 0.5451(3) 0.0551(8) Uani 1 1 d . . . . .
C1 C 0.8297(3) 0.1183(3) 0.4846(3) 0.0398(7) Uani 1 1 d . . . . .
O1 O 0.6396(3) 0.0647(3) 0.4883(3) 0.0948(10) Uani 1 1 d . . . . .
N2 N 1.0171(3) 0.1389(2) 0.6634(2) 0.0522(7) Uani 1 1 d . . . . .
H2A H 1.095960 0.152972 0.694879 0.063 Uiso 1 1 calc R U . . .
H2B H 0.975414 0.123822 0.707076 0.063 Uiso 1 1 calc R U . . .
F2 F 0.80688(18) 0.1573(2) 0.18453(19) 0.0672(6) Uani 1 1 d . . . . .
O2 O 0.7936(3) 0.0881(3) 0.6543(3) 0.0722(8) Uani 1 1 d . . . . .
C2 C 0.9589(3) 0.1403(2) 0.5457(3) 0.0365(7) Uani 1 1 d . . . . .
N3 N 1.0582(2) 0.1878(3) 0.2938(3) 0.0501(7) Uani 1 1 d . . . . .
H3A H 1.136761 0.197881 0.329197 0.060 Uiso 1 1 calc R U . . .
H3B H 1.026481 0.189678 0.218231 0.060 Uiso 1 1 calc R U . . .
F3 F 0.66052(17) 0.1105(2) 0.3005(2) 0.0787(7) Uani 1 1 d . . . . .
C3 C 1.0282(3) 0.1648(3) 0.4770(3) 0.0374(7) Uani 1 1 d . . . . .
C4 C 0.9846(3) 0.1690(2) 0.3566(3) 0.0357(6) Uani 1 1 d . . . . .
C5 C 0.8562(3) 0.1502(3) 0.3019(3) 0.0423(7) Uani 1 1 d . . . . .
C6 C 0.7814(3) 0.1255(3) 0.3621(3) 0.0458(8) Uani 1 1 d . . . . .
O3 O 0.3276(3) 0.1657(3) 0.7753(3) 0.0778(8) Uani 1 1 d . . . . .
F4 F 0.71781(18) 0.33226(17) 0.7494(2) 0.0666(6) Uani 1 1 d . . . . .
N4 N 0.3318(3) 0.2769(3) 0.8139(3) 0.0553(7) Uani 1 1 d . . . . .
O4 O 0.2503(3) 0.3240(3) 0.8513(3) 0.0889(10) Uani 1 1 d . . . . .
N5 N 0.5392(3) 0.1790(3) 0.7364(4) 0.0726(10) Uani 1 1 d . . . . .
H5A H 0.601964 0.154008 0.715530 0.087 Uiso 1 1 calc R U . . .
H5B H 0.482635 0.127256 0.731384 0.087 Uiso 1 1 calc R U . . .
F5 F 0.52190(19) 0.67444(17) 0.8895(2) 0.0656(6) Uani 1 1 d . . . . .
N6 N 0.7181(3) 0.5795(2) 0.8258(3) 0.0539(7) Uani 1 1 d . . . . .
H6A H 0.778835 0.549079 0.804287 0.065 Uiso 1 1 calc R U . . .
H6B H 0.716488 0.657230 0.849950 0.065 Uiso 1 1 calc R U . . .
F6 F 0.33878(18) 0.5342(2) 0.8840(2) 0.0690(6) Uani 1 1 d . . . . .
C7 C 0.4300(3) 0.3515(3) 0.8138(3) 0.0417(7) Uani 1 1 d . . . . .
C8 C 0.5295(3) 0.2997(3) 0.7771(3) 0.0434(7) Uani 1 1 d . . . . .
C9 C 0.6218(3) 0.3808(3) 0.7843(3) 0.0427(7) Uani 1 1 d . . . . .
C10 C 0.6259(3) 0.5058(3) 0.8218(3) 0.0377(7) Uani 1 1 d . . . . .
C11 C 0.5242(3) 0.5520(3) 0.8541(3) 0.0404(7) Uani 1 1 d . . . . .
C12 C 0.4311(3) 0.4790(3) 0.8512(3) 0.0431(7) Uani 1 1 d . . . . .
O5 O 0.7226(2) 0.8312(2) 0.8269(2) 0.0596(6) Uani 1 1 d . . . A 1
O6 O 0.9639(2) 0.8033(2) 0.9584(2) 0.0638(7) Uani 1 1 d . . . A 1
O7 O 0.9755(3) 0.5625(3) 0.8247(3) 0.1004(11) Uani 1 1 d . . . A 1
O8 O 0.8214(7) 0.5018(9) 0.6055(6) 0.094(3) Uani 0.502(13) 1 d D . P A 1
O9 O 0.6826(2) 0.6999(3) 0.5788(3) 0.0694(7) Uani 1 1 d . . . A 1
C13 C 0.7989(4) 0.9269(3) 0.9257(4) 0.0660(11) Uani 1 1 d . . . A 1
H13A H 0.749796 0.980631 0.966664 0.079 Uiso 1 1 calc R U . A 1
H13B H 0.844036 0.973733 0.894318 0.079 Uiso 1 1 calc R U . A 1
C14 C 0.8871(4) 0.8743(3) 1.0169(3) 0.0602(9) Uani 1 1 d . . . A 1
H14A H 0.936739 0.939501 1.089280 0.072 Uiso 1 1 calc R U . A 1
H14B H 0.841788 0.824045 1.044809 0.072 Uiso 1 1 calc R U . A 1
C15 C 1.0203(4) 0.7196(4) 1.0176(4) 0.0741(12) Uani 1 1 d . . . A 1
H15A H 0.960545 0.678199 1.038544 0.089 Uiso 1 1 calc R U . A 1
H15B H 1.085808 0.761856 1.094423 0.089 Uiso 1 1 calc R U . A 1
C16 C 1.0722(4) 0.6279(4) 0.9316(4) 0.0727(11) Uani 1 1 d . . . A 1
H16A H 1.129675 0.669405 0.908116 0.087 Uiso 1 1 calc R U . A 1
H16B H 1.115947 0.572491 0.973925 0.087 Uiso 1 1 calc R U . A 1
C17 C 1.0106(5) 0.4908(5) 0.7287(6) 0.1073(19) Uani 0.5 1 d . . P A 1
H17A H 1.036771 0.416538 0.747150 0.129 Uiso 1 1 calc R U . A 1
H17B H 1.080747 0.533526 0.724227 0.129 Uiso 1 1 calc R U . A 1
C18 C 0.9161(7) 0.4597(5) 0.6105(6) 0.1028(18) Uani 0.502(13) 1 d D . P A 1
H18A H 0.947968 0.483705 0.553280 0.123 Uiso 0.502(13) 1 calc R U P A 1
H18B H 0.898984 0.371637 0.579742 0.123 Uiso 0.502(13) 1 calc R U P A 1
C19 C 0.7549(6) 0.5227(6) 0.4779(6) 0.130(3) Uani 0.502(13) 1 d D . P A 1
H19A H 0.805810 0.576188 0.458925 0.156 Uiso 0.502(13) 1 calc R U P A 1
H19B H 0.730205 0.446434 0.410251 0.156 Uiso 0.502(13) 1 calc R U P A 1
C20 C 0.6523(4) 0.5782(4) 0.5012(4) 0.0827(13) Uani 0.5 1 d . . P A 1
H20A H 0.616168 0.531890 0.540329 0.099 Uiso 1 1 calc R U . A 1
H20B H 0.590925 0.575750 0.422249 0.099 Uiso 1 1 calc R U . A 1
C21 C 0.5879(3) 0.7533(4) 0.6182(4) 0.0700(11) Uani 1 1 d . . . A 1
H21A H 0.546527 0.696564 0.642740 0.084 Uiso 1 1 calc R U . A 1
H21B H 0.528044 0.774414 0.550507 0.084 Uiso 1 1 calc R U . A 1
C22 C 0.6423(3) 0.8660(3) 0.7272(4) 0.0632(10) Uani 1 1 d . . . A 1
H22A H 0.687117 0.921024 0.703858 0.076 Uiso 1 1 calc R U . A 1
H22B H 0.577316 0.907709 0.752581 0.076 Uiso 1 1 calc R U . A 1
O8A O 0.8690(6) 0.5507(5) 0.5549(6) 0.067(3) Uani 0.498(13) 1 d D . P A 2
C17A C 1.0106(5) 0.4908(5) 0.7287(6) 0.1073(19) Uani 0.5 1 d . . P A 2
C18A C 0.9161(7) 0.4597(5) 0.6105(6) 0.1028(18) Uani 0.498(13) 1 d D . P A 2
H18C H 0.946095 0.400903 0.551818 0.123 Uiso 0.498(13) 1 calc R U P A 2
H18D H 0.847115 0.417618 0.617662 0.123 Uiso 0.498(13) 1 calc R U P A 2
C19A C 0.7549(6) 0.5227(6) 0.4779(6) 0.130(3) Uani 0.498(13) 1 d D . P A 2
H19C H 0.736329 0.436087 0.461342 0.156 Uiso 0.498(13) 1 calc R U P A 2
H19D H 0.755832 0.532940 0.399868 0.156 Uiso 0.498(13) 1 calc R U P A 2
C20A C 0.6523(4) 0.5782(4) 0.5012(4) 0.0827(13) Uani 0.5 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.365(3) . ?
N1 O1 1.225(4) . ?
N1 O2 1.235(4) . ?
N1 C1 1.422(4) . ?
C1 C6 1.409(5) . ?
C1 C2 1.418(4) . ?
N2 C2 1.348(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
F2 C5 1.353(4) . ?
C2 C3 1.390(4) . ?
N3 C4 1.348(4) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
F3 C6 1.335(3) . ?
C3 C4 1.371(4) . ?
C4 C5 1.402(4) . ?
C5 C6 1.357(4) . ?
O3 N4 1.226(4) . ?
F4 C9 1.366(3) . ?
N4 O4 1.223(4) . ?
N4 C7 1.422(4) . ?
N5 C8 1.351(4) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
F5 C11 1.354(3) . ?
N6 C10 1.341(4) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
F6 C12 1.344(3) . ?
C7 C12 1.406(4) . ?
C7 C8 1.424(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.375(4) . ?
C10 C11 1.403(4) . ?
C11 C12 1.349(4) . ?
O5 C13 1.398(4) . ?
O5 C22 1.413(4) . ?
O6 C15 1.397(5) . ?
O6 C14 1.411(4) . ?
O7 C17 1.373(6) . ?
O7 C16 1.400(5) . ?
O8 C18 1.186(7) . ?
O8 C19 1.553(9) . ?
O9 C21 1.394(5) . ?
O9 C20 1.408(5) . ?
C13 C14 1.501(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.509(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.419(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.410(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.502(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
O8A C19A 1.315(7) . ?
O8A C18A 1.417(8) . ?
C17A C18A 1.419(8) . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?
C19A C20A 1.410(7) . ?
C19A H19C 0.9700 . ?
C19A H19D 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
O1 N1 O2 120.5(3) . . ?
O1 N1 C1 119.9(3) . . ?
O2 N1 C1 119.7(3) . . ?
C6 C1 C2 118.5(3) . . ?
C6 C1 N1 120.5(3) . . ?
C2 C1 N1 121.0(3) . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N2 C2 C3 119.0(3) . . ?
N2 C2 C1 124.8(3) . . ?
C3 C2 C1 116.3(3) . . ?
C4 N3 H3A 120.0 . . ?
C4 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
F1 C3 C4 117.0(2) . . ?
F1 C3 C2 116.3(3) . . ?
C4 C3 C2 126.7(3) . . ?
N3 C4 C3 123.3(3) . . ?
N3 C4 C5 122.0(3) . . ?
C3 C4 C5 114.7(3) . . ?
F2 C5 C6 119.8(3) . . ?
F2 C5 C4 117.6(3) . . ?
C6 C5 C4 122.5(3) . . ?
F3 C6 C5 116.9(3) . . ?
F3 C6 C1 121.9(3) . . ?
C5 C6 C1 121.2(3) . . ?
O4 N4 O3 119.9(3) . . ?
O4 N4 C7 119.9(3) . . ?
O3 N4 C7 120.3(3) . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C10 N6 H6A 120.0 . . ?
C10 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C12 C7 N4 120.3(3) . . ?
C12 C7 C8 118.4(3) . . ?
N4 C7 C8 121.2(3) . . ?
N5 C8 C9 118.8(3) . . ?
N5 C8 C7 124.9(3) . . ?
C9 C8 C7 116.3(3) . . ?
F4 C9 C10 116.7(3) . . ?
F4 C9 C8 116.9(3) . . ?
C10 C9 C8 126.4(3) . . ?
N6 C10 C9 123.4(3) . . ?
N6 C10 C11 121.6(3) . . ?
C9 C10 C11 114.9(3) . . ?
C12 C11 F5 120.0(3) . . ?
C12 C11 C10 122.3(3) . . ?
F5 C11 C10 117.7(3) . . ?
F6 C12 C11 116.7(3) . . ?
F6 C12 C7 121.7(3) . . ?
C11 C12 C7 121.6(3) . . ?
C13 O5 C22 115.1(3) . . ?
C15 O6 C14 113.8(3) . . ?
C17 O7 C16 115.2(4) . . ?
C18 O8 C19 113.0(7) . . ?
C21 O9 C20 114.8(3) . . ?
O5 C13 C14 108.6(3) . . ?
O5 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
O5 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
O6 C14 C13 109.3(3) . . ?
O6 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
O6 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
O6 C15 C16 109.4(3) . . ?
O6 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
O6 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
O7 C16 C15 109.0(3) . . ?
O7 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
O7 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O7 C17 C18 113.6(4) . . ?
O7 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
O7 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
O8 C18 C17 117.7(5) . . ?
O8 C18 H18A 107.9 . . ?
C17 C18 H18A 107.9 . . ?
O8 C18 H18B 107.9 . . ?
C17 C18 H18B 107.9 . . ?
H18A C18 H18B 107.2 . . ?
C20 C19 O8 100.6(5) . . ?
C20 C19 H19A 111.7 . . ?
O8 C19 H19A 111.7 . . ?
C20 C19 H19B 111.7 . . ?
O8 C19 H19B 111.7 . . ?
H19A C19 H19B 109.4 . . ?
C19 C20 O9 112.8(4) . . ?
C19 C20 H20A 109.0 . . ?
O9 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
O9 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
O9 C21 C22 108.6(3) . . ?
O9 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
O9 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
O5 C22 C21 108.5(3) . . ?
O5 C22 H22A 110.0 . . ?
C21 C22 H22A 110.0 . . ?
O5 C22 H22B 110.0 . . ?
C21 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C19A O8A C18A 114.1(6) . . ?
O8A C18A C17A 120.7(5) . . ?
O8A C18A H18C 107.1 . . ?
C17A C18A H18C 107.1 . . ?
O8A C18A H18D 107.1 . . ?
C17A C18A H18D 107.1 . . ?
H18C C18A H18D 106.8 . . ?
O8A C19A C20A 125.0(5) . . ?
O8A C19A H19C 106.1 . . ?
C20A C19A H19C 106.1 . . ?
O8A C19A H19D 106.1 . . ?
C20A C19A H19D 106.1 . . ?
H19C C19A H19D 106.3 . . ?

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
O1 N1 C1 C6 3.5(5) . . . . ?
O2 N1 C1 C6 -177.1(3) . . . . ?
O1 N1 C1 C2 -176.4(3) . . . . ?
O2 N1 C1 C2 3.0(4) . . . . ?
C6 C1 C2 N2 178.6(3) . . . . ?
N1 C1 C2 N2 -1.6(4) . . . . ?
C6 C1 C2 C3 -1.4(4) . . . . ?
N1 C1 C2 C3 178.4(3) . . . . ?
N2 C2 C3 F1 1.3(4) . . . . ?
C1 C2 C3 F1 -178.7(2) . . . . ?
N2 C2 C3 C4 179.5(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
F1 C3 C4 N3 1.5(4) . . . . ?
C2 C3 C4 N3 -176.8(3) . . . . ?
F1 C3 C4 C5 -179.5(2) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
N3 C4 C5 F2 -3.1(4) . . . . ?
C3 C4 C5 F2 177.8(3) . . . . ?
N3 C4 C5 C6 176.9(3) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
F2 C5 C6 F3 -0.6(4) . . . . ?
C4 C5 C6 F3 179.4(3) . . . . ?
F2 C5 C6 C1 -179.6(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C2 C1 C6 F3 -177.4(3) . . . . ?
N1 C1 C6 F3 2.7(5) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
N1 C1 C6 C5 -178.4(3) . . . . ?
O4 N4 C7 C12 -2.9(5) . . . . ?
O3 N4 C7 C12 176.3(3) . . . . ?
O4 N4 C7 C8 176.6(3) . . . . ?
O3 N4 C7 C8 -4.2(5) . . . . ?
C12 C7 C8 N5 -178.4(3) . . . . ?
N4 C7 C8 N5 2.1(5) . . . . ?
C12 C7 C8 C9 1.4(4) . . . . ?
N4 C7 C8 C9 -178.1(3) . . . . ?
N5 C8 C9 F4 -0.2(5) . . . . ?
C7 C8 C9 F4 -180.0(3) . . . . ?
N5 C8 C9 C10 179.0(3) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
F4 C9 C10 N6 -0.4(5) . . . . ?
C8 C9 C10 N6 -179.5(3) . . . . ?
F4 C9 C10 C11 178.6(3) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
N6 C10 C11 C12 -179.6(3) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
N6 C10 C11 F5 0.2(4) . . . . ?
C9 C10 C11 F5 -178.8(3) . . . . ?
F5 C11 C12 F6 0.3(4) . . . . ?
C10 C11 C12 F6 -179.9(3) . . . . ?
F5 C11 C12 C7 179.4(3) . . . . ?
C10 C11 C12 C7 -0.8(5) . . . . ?
N4 C7 C12 F6 -2.2(5) . . . . ?
C8 C7 C12 F6 178.3(3) . . . . ?
N4 C7 C12 C11 178.8(3) . . . . ?
C8 C7 C12 C11 -0.7(5) . . . . ?
C22 O5 C13 C14 -174.1(3) . . . . ?
C15 O6 C14 C13 -160.1(3) . . . . ?
O5 C13 C14 O6 63.8(4) . . . . ?
C14 O6 C15 C16 165.4(3) . . . . ?
C17 O7 C16 C15 169.1(4) . . . . ?
O6 C15 C16 O7 -63.1(5) . . . . ?
C16 O7 C17 C18 -159.7(5) . . . . ?
C19 O8 C18 C17 149.2(6) . . . . ?
O7 C17 C18 O8 3.4(10) . . . . ?
C18 O8 C19 C20 -176.8(8) . . . . ?
O8 C19 C20 O9 74.5(6) . . . . ?
C21 O9 C20 C19 -171.7(5) . . . . ?
C20 O9 C21 C22 163.5(3) . . . . ?
C13 O5 C22 C21 167.6(3) . . . . ?
O9 C21 C22 O5 -63.5(4) . . . . ?
C19A O8A C18A C17A -153.2(6) . . . . ?
C18A O8A C19A C20A 109.6(8) . . . . ?

_refine_diff_density_max         0.493
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.060


####################################################################### 
# 
# 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_M412_B15cr5
_database_code_depnum_ccdc_archive 'CCDC 2362726'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2024-06-14 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
Co-crystal of 2,4-diaminotrifluoropyridine and 15-crown-5, 1:1
;
_chemical_name_common            ?
_chemical_melting_point          367
_chemical_formula_moiety         'C5 H4 F3 N3, C10 H20 O5'
_chemical_formula_sum            'C15 H24 F3 N3 O5'
_chemical_formula_weight         383.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   24.7949(15)
_cell_length_b                   8.4611(4)
_cell_length_c                   17.9811(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.929(3)
_cell_angle_gamma                90
_cell_volume                     3770.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8685
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      23.76

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9514
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32775
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.644
_diffrn_reflns_theta_max         25.474
_diffrn_reflns_theta_full        25.000
_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             3496
_reflns_number_gt                2349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²+8.4991P] 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         3496
_refine_ls_number_parameters     259
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.2165
_refine_ls_wR_factor_gt          0.1860
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.82598(8) 0.4799(2) 0.86586(10) 0.0653(6) Uani 1 1 d . . . A 1
F2 F 0.93276(10) 0.8692(3) 0.75442(13) 0.0759(9) Uani 0.892(5) 1 d . . P A 1
F3 F 0.94370(12) 1.0065(3) 0.88738(16) 0.1029(9) Uani 1 1 d . . . A 1
N1 N 0.89418(12) 0.8187(3) 0.94246(16) 0.0591(7) Uani 1 1 d . . . A 1
N2 N 0.84206(13) 0.6324(4) 1.00044(15) 0.0713(9) Uani 1 1 d . . . A 1
H2A H 0.846557 0.683476 1.041522 0.086 Uiso 1 1 calc R U . A 1
H2B H 0.823053 0.547312 0.999103 0.086 Uiso 1 1 calc R U . A 1
N3 N 0.86828(15) 0.6028(4) 0.73754(16) 0.0805(11) Uani 1 1 d . . . A 1
H3A H 0.848812 0.518844 0.733894 0.097 Uiso 1 1 calc R U . A 1
H3B H 0.881956 0.642966 0.698490 0.097 Uiso 1 1 calc R U . A 1
C2 C 0.86496(12) 0.6859(4) 0.93769(16) 0.0453(7) Uani 1 1 d . . . A 1
C3 C 0.85677(11) 0.6136(3) 0.86960(16) 0.0410(7) Uani 1 1 d . . . A 1
C4 C 0.87733(12) 0.6710(3) 0.80416(16) 0.0434(7) Uani 1 1 d . . . A 1
C5 C 0.90834(12) 0.8068(4) 0.81265(18) 0.0482(8) Uani 1 1 d . . . A 1
C6 C 0.91431(14) 0.8719(4) 0.8806(2) 0.0576(9) Uani 1 1 d . . . A 1
F2A F 0.9221(8) 0.883(2) 0.9954(10) 0.068(7) Uiso 0.108(5) 1 d . . P A 2
O1 O 0.78977(11) 0.3501(3) 0.07452(15) 0.0728(8) Uani 1 1 d . . . . .
O2 O 0.89910(12) 0.2748(4) 0.09047(15) 0.0863(9) Uani 1 1 d . . . . .
O5 O 0.78488(11) 0.6146(3) 0.17108(15) 0.0782(8) Uani 1 1 d . . . . .
O4 O 0.88172(13) 0.7745(4) 0.14729(19) 0.1030(11) Uani 1 1 d D . . . .
C15 C 0.74006(15) 0.5551(6) 0.1303(2) 0.0795(12) Uani 1 1 d . . . . .
H15A H 0.737403 0.605355 0.081848 0.095 Uiso 1 1 calc R U . . .
H15B H 0.707259 0.577494 0.156280 0.095 Uiso 1 1 calc R U . . .
C16 C 0.74647(15) 0.3826(5) 0.1214(2) 0.0752(11) Uani 1 1 d . . . . .
H16A H 0.753427 0.334224 0.169712 0.090 Uiso 1 1 calc R U . . .
H16B H 0.713431 0.337769 0.100085 0.090 Uiso 1 1 calc R U . . .
C7 C 0.8084(2) 0.1948(5) 0.0774(3) 0.0823(12) Uani 1 1 d . . . . .
H7A H 0.783562 0.126628 0.049577 0.099 Uiso 1 1 calc R U . . .
H7B H 0.810395 0.158713 0.128581 0.099 Uiso 1 1 calc R U . . .
C8 C 0.8629(2) 0.1866(5) 0.0449(2) 0.0826(12) Uani 1 1 d . . . . .
H8A H 0.874717 0.077576 0.042471 0.099 Uiso 1 1 calc R U . . .
H8B H 0.861515 0.229605 -0.005106 0.099 Uiso 1 1 calc R U . . .
C13 C 0.8454(2) 0.8211(5) 0.1984(2) 0.0844(13) Uani 1 1 d . . . . .
H13A H 0.848017 0.934349 0.206261 0.101 Uiso 1 1 calc R U . . .
H13B H 0.853160 0.768776 0.245566 0.101 Uiso 1 1 calc R U . . .
C14 C 0.79023(18) 0.7796(5) 0.1707(2) 0.0775(12) Uani 1 1 d . . . . .
H14A H 0.763707 0.826864 0.202313 0.093 Uiso 1 1 calc R U . . .
H14B H 0.784218 0.819713 0.120555 0.093 Uiso 1 1 calc R U . . .
O3 O 0.95494(15) 0.5656(6) 0.0896(3) 0.1444(17) Uani 1 1 d D . . . .
C10 C 0.9787(2) 0.4241(7) 0.1022(4) 0.1089(18) Uani 1 1 d . . . . .
H10A H 0.979272 0.401012 0.155014 0.131 Uiso 1 1 calc R U . . .
H10B H 1.015701 0.427772 0.086353 0.131 Uiso 1 1 calc R U . . .
C9 C 0.9498(2) 0.3006(7) 0.0619(3) 0.1107(18) Uani 1 1 d . . . . .
H9A H 0.945704 0.329992 0.009912 0.133 Uiso 1 1 calc R U . . .
H9B H 0.970509 0.203523 0.064956 0.133 Uiso 1 1 calc R U . . .
C12 C 0.9357(3) 0.7532(12) 0.1822(5) 0.072(3) Uani 0.531(17) 1 d D U P B 1
H12A H 0.948586 0.851327 0.204366 0.086 Uiso 0.531(17) 1 calc R U P B 1
H12B H 0.935068 0.672709 0.220543 0.086 Uiso 0.531(17) 1 calc R U P B 1
C11 C 0.9705(4) 0.7042(12) 0.1215(6) 0.077(3) Uani 0.531(17) 1 d D U P B 1
H11A H 0.970027 0.786082 0.083740 0.092 Uiso 0.531(17) 1 calc R U P B 1
H11B H 1.007257 0.693914 0.140985 0.092 Uiso 0.531(17) 1 calc R U P B 1
C12A C 0.9386(5) 0.8040(16) 0.1492(10) 0.106(5) Uani 0.469(17) 1 d D U P B 2
H12C H 0.948392 0.870579 0.191385 0.128 Uiso 0.469(17) 1 calc R U P B 2
H12D H 0.948514 0.858217 0.104117 0.128 Uiso 0.469(17) 1 calc R U P B 2
C11A C 0.9683(6) 0.6459(19) 0.1556(9) 0.114(5) Uani 0.469(17) 1 d D U P B 2
H11C H 1.006968 0.662389 0.160564 0.137 Uiso 0.469(17) 1 calc R U P B 2
H11D H 0.956577 0.586840 0.198352 0.137 Uiso 0.469(17) 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.366(3) . ?
F2 C5 1.336(4) . ?
F3 C6 1.355(4) . ?
N1 C6 1.314(4) . ?
N1 C2 1.338(4) . ?
N2 C2 1.358(4) . ?
N3 C4 1.342(4) . ?
C2 C3 1.378(4) . ?
C3 C4 1.386(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.344(5) . ?
O1 C7 1.392(5) . ?
O1 C16 1.414(5) . ?
O2 C9 1.390(5) . ?
O2 C8 1.409(5) . ?
O5 C14 1.403(5) . ?
O5 C15 1.404(5) . ?
O4 C13 1.367(5) . ?
O4 C12A 1.431(12) . ?
O4 C12 1.470(9) . ?
C15 C16 1.478(6) . ?
C7 C8 1.491(6) . ?
C13 C14 1.482(6) . ?
O3 C10 1.349(6) . ?
O3 C11 1.356(8) . ?
O3 C11A 1.397(12) . ?
C10 C9 1.447(8) . ?
C12 C11 1.472(12) . ?
C12A C11A 1.530(17) . ?

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 N1 C2 117.0(3) . . ?
N1 C2 N2 117.9(3) . . ?
N1 C2 C3 119.5(3) . . ?
N2 C2 C3 122.5(3) . . ?
F1 C3 C2 118.5(2) . . ?
F1 C3 C4 118.0(2) . . ?
C2 C3 C4 123.5(3) . . ?
N3 C4 C3 123.5(3) . . ?
N3 C4 C5 122.0(3) . . ?
C3 C4 C5 114.5(3) . . ?
F2 C5 C6 120.8(3) . . ?
F2 C5 C4 120.3(3) . . ?
C6 C5 C4 118.9(3) . . ?
N1 C6 C5 126.6(3) . . ?
N1 C6 F3 115.5(3) . . ?
C5 C6 F3 117.9(3) . . ?
C7 O1 C16 114.8(3) . . ?
C9 O2 C8 115.8(4) . . ?
C14 O5 C15 115.3(3) . . ?
C13 O4 C12A 127.2(7) . . ?
C13 O4 C12 111.1(5) . . ?
O5 C15 C16 108.9(3) . . ?
O1 C16 C15 110.1(3) . . ?
O1 C7 C8 109.5(4) . . ?
O2 C8 C7 108.5(3) . . ?
O4 C13 C14 109.1(3) . . ?
O5 C14 C13 108.7(3) . . ?
C10 O3 C11 125.5(7) . . ?
C10 O3 C11A 101.5(8) . . ?
O3 C10 C9 110.5(5) . . ?
O2 C9 C10 111.6(4) . . ?
C11 C12 O4 105.4(8) . . ?
O3 C11 C12 113.1(8) . . ?
O4 C12A C11A 108.8(12) . . ?
O3 C11A C12A 105.2(12) . . ?

_refine_diff_density_max         0.726
_refine_diff_density_min         -0.457
_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_t7021_4_2C12cr4
_database_code_depnum_ccdc_archive 'CCDC 2362729'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2024-06-14 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
Co-crystal of 2,4-diaminotrifluoronitrobenzene and 12-crown-4, 2:1
;
_chemical_name_common            ?
_chemical_melting_point          403
_chemical_formula_moiety         '2(C6 H4 F3 N3 O2), C8 H16 O4'
_chemical_formula_sum            'C20 H24 F6 N6 O8'
_chemical_formula_weight         590.45

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                   15.4617(18)
_cell_length_b                   21.673(3)
_cell_length_c                   7.3234(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.584(5)
_cell_angle_gamma                90
_cell_volume                     2454.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      23.77

_exptl_crystal_description       prismoid
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8028
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_process_details   SADABS-2016/2
_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            43266
_diffrn_reflns_av_unetI/netI     0.1265
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.317
_diffrn_reflns_theta_max         26.219
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4876
_reflns_number_gt                2325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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         4876
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1992
_refine_ls_R_factor_gt           0.1404
_refine_ls_wR_factor_ref         0.4467
_refine_ls_wR_factor_gt          0.4282
_refine_ls_goodness_of_fit_ref   1.363
_refine_ls_restrained_S_all      1.363
_refine_ls_shift/su_max          0.004
_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 0.8143(3) 0.60683(18) 0.4164(6) 0.0607(13) Uani 1 1 d . . . . .
N1 N 0.7083(5) 0.8112(3) 0.5182(10) 0.0602(19) Uani 1 1 d . . . . .
C1 C 0.7730(5) 0.7710(3) 0.4572(10) 0.0414(17) Uani 1 1 d . . . . .
O1 O 0.6371(5) 0.7930(3) 0.5550(11) 0.093(2) Uani 1 1 d . . . . .
N2 N 0.6834(4) 0.6786(3) 0.5121(10) 0.0595(18) Uani 1 1 d . . . . .
H2A H 0.678499 0.639042 0.512029 0.071 Uiso 1 1 calc R U . . .
H2B H 0.640616 0.701200 0.544901 0.071 Uiso 1 1 calc R U . . .
F2 F 0.9937(3) 0.7760(2) 0.2937(8) 0.0794(17) Uani 1 1 d . . . . .
O2 O 0.7241(5) 0.8668(3) 0.5322(12) 0.093(2) Uani 1 1 d . . . . .
C2 C 0.7581(5) 0.7050(3) 0.4609(10) 0.0450(18) Uani 1 1 d . . . . .
N3 N 0.9714(5) 0.6512(3) 0.3069(11) 0.071(2) Uani 1 1 d . . . . .
H3A H 0.963549 0.611902 0.308671 0.085 Uiso 1 1 calc R U . . .
H3B H 1.020503 0.666023 0.274415 0.085 Uiso 1 1 calc R U . . .
F3 F 0.8688(4) 0.8531(2) 0.3836(8) 0.0796(17) Uani 1 1 d . . . . .
C3 C 0.8270(5) 0.6697(3) 0.4082(10) 0.0453(18) Uani 1 1 d . . . . .
C4 C 0.9067(5) 0.6895(3) 0.3551(10) 0.0446(18) Uani 1 1 d . . . . .
C5 C 0.9178(5) 0.7537(4) 0.3539(12) 0.052(2) Uani 1 1 d . . . . .
C6 C 0.8535(5) 0.7922(3) 0.4009(11) 0.053(2) Uani 1 1 d . . . . .
O5 O 0.5098(5) 0.5121(3) 0.2466(8) 0.080(2) Uani 1 1 d . . . . .
O6 O 0.3690(5) 0.4501(3) 0.4604(12) 0.106(3) Uani 1 1 d . . . . .
C13 C 0.4768(10) 0.4558(5) 0.2195(17) 0.119(5) Uani 1 1 d . . . . .
H13A H 0.502754 0.426374 0.303636 0.142 Uiso 1 1 calc R U . . .
H13B H 0.487349 0.442065 0.095647 0.142 Uiso 1 1 calc R U . . .
C14 C 0.3823(6) 0.4614(5) 0.2525(12) 0.072(3) Uani 1 1 d . . . . .
H14A H 0.350642 0.430997 0.181139 0.086 Uiso 1 1 calc R U . . .
H14B H 0.361998 0.502154 0.218386 0.086 Uiso 1 1 calc R U . . .
C15 C 0.3571(8) 0.5051(5) 0.5523(17) 0.100(4) Uani 1 1 d . . . . .
H15A H 0.296268 0.515881 0.558080 0.120 Uiso 1 1 calc R U . . .
H15B H 0.388476 0.538529 0.494999 0.120 Uiso 1 1 calc R U . . .
C16 C 0.3923(7) 0.4912(5) 0.7336(14) 0.083(3) Uani 1 1 d . . . . .
H16A H 0.368657 0.451974 0.772419 0.100 Uiso 1 1 calc R U . . .
H16B H 0.371545 0.522388 0.817423 0.100 Uiso 1 1 calc R U . . .
O7 O -0.1211(4) 1.0505(3) 0.4620(9) 0.0755(19) Uani 1 1 d . . . . .
O8 O -0.0264(5) 0.9857(3) 0.7650(8) 0.0731(19) Uani 1 1 d . . . . .
C17 C -0.1584(6) 1.0152(6) 0.5944(14) 0.090(4) Uani 1 1 d . . . . .
H17A H -0.157599 0.972044 0.559548 0.108 Uiso 1 1 calc R U . . .
H17B H -0.217960 1.027682 0.612062 0.108 Uiso 1 1 calc R U . . .
C18 C -0.1071(6) 1.0247(5) 0.7657(12) 0.071(3) Uani 1 1 d . . . . .
H18A H -0.091329 1.067908 0.776672 0.085 Uiso 1 1 calc R U . . .
H18B H -0.142024 1.013864 0.870146 0.085 Uiso 1 1 calc R U . . .
C19 C 0.0448(6) 1.0195(5) 0.7439(15) 0.083(3) Uani 1 1 d . . . . .
H19A H 0.052384 1.046095 0.849459 0.100 Uiso 1 1 calc R U . . .
H19B H 0.037658 1.045700 0.637300 0.100 Uiso 1 1 calc R U . . .
C20 C 0.1209(6) 0.9822(4) 0.7225(11) 0.063(2) Uani 1 1 d . . . . .
H20A H 0.123444 0.951728 0.819444 0.076 Uiso 1 1 calc R U . . .
H20B H 0.171868 1.008101 0.733152 0.076 Uiso 1 1 calc R U . . .
O3 O 0.1359(5) 0.7069(3) 0.4753(13) 0.102(3) Uani 1 1 d . . . . .
F4 F 0.3143(3) 0.89403(18) 0.6148(6) 0.0591(13) Uani 1 1 d . . . . .
O4 O 0.2227(5) 0.6334(3) 0.5125(13) 0.100(3) Uani 1 1 d . . . . .
N4 N 0.2060(5) 0.6884(3) 0.5233(9) 0.0562(18) Uani 1 1 d . . . . .
N5 N 0.1822(4) 0.8218(3) 0.5151(10) 0.063(2) Uani 1 1 d . . . . .
H5A H 0.178865 0.861380 0.508323 0.076 Uiso 1 1 calc R U . . .
H5B H 0.138343 0.799488 0.485047 0.076 Uiso 1 1 calc R U . . .
F5 F 0.4952(3) 0.7248(2) 0.7377(8) 0.0752(16) Uani 1 1 d . . . . .
N6 N 0.4731(4) 0.8492(3) 0.7254(10) 0.067(2) Uani 1 1 d . . . . .
H6A H 0.465644 0.888500 0.726494 0.080 Uiso 1 1 calc R U . . .
H6B H 0.522215 0.833761 0.757103 0.080 Uiso 1 1 calc R U . . .
F6 F 0.3696(3) 0.6477(2) 0.6515(8) 0.0794(17) Uani 1 1 d . . . . .
C7 C 0.2718(5) 0.7297(3) 0.5781(10) 0.0432(18) Uani 1 1 d . . . . .
C8 C 0.2572(4) 0.7945(3) 0.5737(11) 0.0443(18) Uani 1 1 d . . . . .
C9 C 0.3275(5) 0.8326(3) 0.6216(10) 0.0425(18) Uani 1 1 d . . . . .
C10 C 0.4076(4) 0.8117(3) 0.6740(10) 0.0447(18) Uani 1 1 d . . . . .
C11 C 0.4182(5) 0.7473(4) 0.6814(11) 0.050(2) Uani 1 1 d . . . . .
C12 C 0.3529(5) 0.7082(3) 0.6326(11) 0.051(2) 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 C3 1.378(8) . ?
N1 O1 1.203(9) . ?
N1 O2 1.233(9) . ?
N1 C1 1.403(10) . ?
C1 C6 1.394(11) . ?
C1 C2 1.448(10) . ?
N2 C2 1.346(9) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
F2 C5 1.348(9) . ?
C2 C3 1.370(10) . ?
N3 C4 1.351(10) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
F3 C6 1.346(8) . ?
C3 C4 1.366(10) . ?
C4 C5 1.401(11) . ?
C5 C6 1.345(11) . ?
O5 C13 1.337(14) . ?
O5 C16 1.520(12) 3_666 ?
O6 C15 1.383(12) . ?
O6 C14 1.558(12) . ?
C13 C14 1.488(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.461(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O7 C17 1.367(11) . ?
O7 C20 1.526(11) 3_576 ?
O8 C19 1.333(11) . ?
O8 C18 1.507(11) . ?
C17 C18 1.492(14) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.438(13) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
O3 N4 1.205(9) . ?
F4 C9 1.347(7) . ?
O4 N4 1.222(9) . ?
N4 C7 1.410(10) . ?
N5 C8 1.368(9) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
F5 C11 1.347(8) . ?
N6 C10 1.348(10) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
F6 C12 1.343(8) . ?
C7 C12 1.391(10) . ?
C7 C8 1.423(10) . ?
C8 C9 1.407(10) . ?
C9 C10 1.371(10) . ?
C10 C11 1.407(11) . ?
C11 C12 1.363(11) . ?

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
O1 N1 O2 119.0(7) . . ?
O1 N1 C1 121.6(7) . . ?
O2 N1 C1 119.5(8) . . ?
C6 C1 N1 122.1(7) . . ?
C6 C1 C2 118.2(7) . . ?
N1 C1 C2 119.6(7) . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N2 C2 C3 120.8(7) . . ?
N2 C2 C1 124.2(7) . . ?
C3 C2 C1 115.0(7) . . ?
C4 N3 H3A 120.0 . . ?
C4 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C2 C3 C4 127.6(7) . . ?
C2 C3 F1 115.4(6) . . ?
C4 C3 F1 117.0(6) . . ?
N3 C4 C3 123.6(7) . . ?
N3 C4 C5 121.2(7) . . ?
C3 C4 C5 115.2(7) . . ?
C6 C5 F2 120.6(7) . . ?
C6 C5 C4 121.5(7) . . ?
F2 C5 C4 117.7(7) . . ?
C5 C6 F3 116.9(8) . . ?
C5 C6 C1 122.4(7) . . ?
F3 C6 C1 120.6(7) . . ?
C13 O5 C16 110.4(9) . 3_666 ?
C15 O6 C14 111.1(8) . . ?
O5 C13 C14 106.0(9) . . ?
O5 C13 H13A 110.5 . . ?
C14 C13 H13A 110.5 . . ?
O5 C13 H13B 110.5 . . ?
C14 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 O6 106.6(8) . . ?
C13 C14 H14A 110.4 . . ?
O6 C14 H14A 110.4 . . ?
C13 C14 H14B 110.4 . . ?
O6 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
O6 C15 C16 102.3(10) . . ?
O6 C15 H15A 111.3 . . ?
C16 C15 H15A 111.3 . . ?
O6 C15 H15B 111.3 . . ?
C16 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C15 C16 O5 117.3(8) . 3_666 ?
C15 C16 H16A 108.0 . . ?
O5 C16 H16A 108.0 3_666 . ?
C15 C16 H16B 108.0 . . ?
O5 C16 H16B 108.0 3_666 . ?
H16A C16 H16B 107.2 . . ?
C17 O7 C20 111.9(8) . 3_576 ?
C19 O8 C18 112.1(7) . . ?
O7 C17 C18 107.1(9) . . ?
O7 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
O7 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.5 . . ?
O8 C18 C17 110.6(7) . . ?
O8 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
O8 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
O8 C19 C20 112.4(9) . . ?
O8 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
O8 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 O7 111.5(7) . 3_576 ?
C19 C20 H20A 109.3 . . ?
O7 C20 H20A 109.3 3_576 . ?
C19 C20 H20B 109.3 . . ?
O7 C20 H20B 109.3 3_576 . ?
H20A C20 H20B 108.0 . . ?
O3 N4 O4 119.7(7) . . ?
O3 N4 C7 121.1(7) . . ?
O4 N4 C7 118.9(7) . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C10 N6 H6A 120.0 . . ?
C10 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C12 C7 C8 118.6(7) . . ?
C12 C7 N4 121.0(7) . . ?
C8 C7 N4 120.4(7) . . ?
N5 C8 C9 118.3(7) . . ?
N5 C8 C7 124.7(7) . . ?
C9 C8 C7 116.9(6) . . ?
F4 C9 C10 118.3(6) . . ?
F4 C9 C8 117.1(6) . . ?
C10 C9 C8 124.7(6) . . ?
N6 C10 C9 123.6(7) . . ?
N6 C10 C11 120.0(7) . . ?
C9 C10 C11 116.3(6) . . ?
F5 C11 C12 120.4(7) . . ?
F5 C11 C10 118.2(7) . . ?
C12 C11 C10 121.3(7) . . ?
C11 C12 F6 116.0(7) . . ?
C11 C12 C7 122.1(7) . . ?
F6 C12 C7 121.8(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C6 175.0(8) . . . . ?
O2 N1 C1 C6 -4.0(11) . . . . ?
O1 N1 C1 C2 -8.3(11) . . . . ?
O2 N1 C1 C2 172.7(7) . . . . ?
C6 C1 C2 N2 -179.9(7) . . . . ?
N1 C1 C2 N2 3.3(11) . . . . ?
C6 C1 C2 C3 0.4(10) . . . . ?
N1 C1 C2 C3 -176.5(7) . . . . ?
N2 C2 C3 C4 -179.2(7) . . . . ?
C1 C2 C3 C4 0.6(11) . . . . ?
N2 C2 C3 F1 -1.5(10) . . . . ?
C1 C2 C3 F1 178.2(6) . . . . ?
C2 C3 C4 N3 179.3(8) . . . . ?
F1 C3 C4 N3 1.7(11) . . . . ?
C2 C3 C4 C5 -0.5(11) . . . . ?
F1 C3 C4 C5 -178.1(6) . . . . ?
N3 C4 C5 C6 179.7(8) . . . . ?
C3 C4 C5 C6 -0.5(11) . . . . ?
N3 C4 C5 F2 3.5(11) . . . . ?
C3 C4 C5 F2 -176.7(7) . . . . ?
F2 C5 C6 F3 0.4(11) . . . . ?
C4 C5 C6 F3 -175.7(7) . . . . ?
F2 C5 C6 C1 177.5(7) . . . . ?
C4 C5 C6 C1 1.4(12) . . . . ?
N1 C1 C6 C5 175.4(7) . . . . ?
C2 C1 C6 C5 -1.3(11) . . . . ?
N1 C1 C6 F3 -7.6(11) . . . . ?
C2 C1 C6 F3 175.7(6) . . . . ?
C16 O5 C13 C14 165.0(8) 3_666 . . . ?
O5 C13 C14 O6 -88.4(10) . . . . ?
C15 O6 C14 C13 101.8(11) . . . . ?
C14 O6 C15 C16 -150.3(8) . . . . ?
O6 C15 C16 O5 74.6(12) . . . 3_666 ?
C20 O7 C17 C18 141.4(8) 3_576 . . . ?
C19 O8 C18 C17 108.7(10) . . . . ?
O7 C17 C18 O8 -80.5(11) . . . . ?
C18 O8 C19 C20 -173.5(7) . . . . ?
O8 C19 C20 O7 70.7(11) . . . 3_576 ?
O3 N4 C7 C12 -179.7(8) . . . . ?
O4 N4 C7 C12 -4.9(12) . . . . ?
O3 N4 C7 C8 -1.4(12) . . . . ?
O4 N4 C7 C8 173.4(8) . . . . ?
C12 C7 C8 N5 176.9(8) . . . . ?
N4 C7 C8 N5 -1.4(11) . . . . ?
C12 C7 C8 C9 1.4(10) . . . . ?
N4 C7 C8 C9 -176.9(7) . . . . ?
N5 C8 C9 F4 3.2(10) . . . . ?
C7 C8 C9 F4 179.0(6) . . . . ?
N5 C8 C9 C10 -176.7(7) . . . . ?
C7 C8 C9 C10 -1.0(11) . . . . ?
F4 C9 C10 N6 2.5(11) . . . . ?
C8 C9 C10 N6 -177.6(7) . . . . ?
F4 C9 C10 C11 179.2(6) . . . . ?
C8 C9 C10 C11 -0.9(11) . . . . ?
N6 C10 C11 F5 -1.1(11) . . . . ?
C9 C10 C11 F5 -178.0(7) . . . . ?
N6 C10 C11 C12 179.1(8) . . . . ?
C9 C10 C11 C12 2.3(11) . . . . ?
F5 C11 C12 F6 2.5(12) . . . . ?
C10 C11 C12 F6 -177.8(7) . . . . ?
F5 C11 C12 C7 178.4(7) . . . . ?
C10 C11 C12 C7 -1.9(13) . . . . ?
C8 C7 C12 C11 -0.1(12) . . . . ?
N4 C7 C12 C11 178.2(7) . . . . ?
C8 C7 C12 F6 175.6(7) . . . . ?
N4 C7 C12 F6 -6.1(12) . . . . ?

_refine_diff_density_max         0.913
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.114




####################################################################### 
# 
# 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_m403_2B12cr4
_database_code_depnum_ccdc_archive 'CCDC 2362728'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2024-06-14 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
Co-crystal of 2,4-diaminotrifluoropyridine and 12-crown-4, 2:1
;
_chemical_name_common            ?
_chemical_melting_point          351
_chemical_formula_moiety         '2(C5 H4 F3 N3), C8 H16 O4'
_chemical_formula_sum            'C18 H24 F6 N6 O4'
_chemical_formula_weight         502.43

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      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                   5.7104(2)
_cell_length_b                   9.5020(4)
_cell_length_c                   10.2481(5)
_cell_angle_alpha                88.963(2)
_cell_angle_beta                 87.032(2)
_cell_angle_gamma                81.176(2)
_cell_volume                     548.72(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8454
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      29.17

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9323
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19664
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.929
_diffrn_reflns_theta_max         29.171
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2944
_reflns_number_gt                2344
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.0857P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2944
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
N1 N 0.25410(17) 0.04963(10) 0.89628(9) 0.0435(2) Uani 1 1 d . . . . .
F1 F 0.40206(16) 0.36683(8) 1.03695(8) 0.0631(2) Uani 1 1 d . . . . .
N2 N 0.0830(2) 0.17836(14) 1.07611(11) 0.0581(3) Uani 1 1 d . . . . .
H1 H -0.016(3) 0.1125(17) 1.0835(14) 0.056(4) Uiso 1 1 d . . . . .
H2 H 0.086(3) 0.2375(18) 1.1320(16) 0.062(4) Uiso 1 1 d . . . . .
F2 F 0.73768(15) 0.10145(9) 0.66925(7) 0.0625(2) Uani 1 1 d . . . . .
C2 C 0.2499(2) 0.16119(11) 0.97601(10) 0.0397(2) Uani 1 1 d . . . . .
N3 N 0.7330(2) 0.33707(12) 0.82728(12) 0.0546(3) Uani 1 1 d . . . . .
H3 H 0.731(3) 0.4056(18) 0.8793(16) 0.064(4) Uiso 1 1 d . . . . .
H4 H 0.841(3) 0.3249(16) 0.7659(16) 0.061(4) Uiso 1 1 d . . . . .
F3 F 0.41841(16) -0.07786(9) 0.72292(8) 0.0672(3) Uani 1 1 d . . . . .
C3 C 0.4116(2) 0.25492(11) 0.95423(10) 0.0410(2) Uani 1 1 d . . . . .
C4 C 0.58167(19) 0.24168(11) 0.85192(10) 0.0393(2) Uani 1 1 d . . . . .
C5 C 0.5792(2) 0.12389(12) 0.77267(10) 0.0422(3) Uani 1 1 d . . . . .
C6 C 0.4166(2) 0.03583(12) 0.80018(11) 0.0435(3) Uani 1 1 d . . . . .
O1 O 0.11204(15) 0.33406(9) 0.60755(8) 0.0482(2) Uani 1 1 d . . . . .
O2 O 0.01238(16) 0.36000(9) 0.32267(8) 0.0491(2) Uani 1 1 d . . . . .
C7 C 0.2686(2) 0.43669(12) 0.59681(12) 0.0451(3) Uani 1 1 d . . . . .
H7A H 0.259300 0.482332 0.511406 0.054 Uiso 1 1 calc R U . . .
H7B H 0.430504 0.390417 0.606362 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1594(2) 0.22500(13) 0.51151(12) 0.0493(3) Uani 1 1 d . . . . .
H8A H 0.158997 0.132921 0.553897 0.059 Uiso 1 1 calc R U . . .
H8B H 0.315900 0.226422 0.470452 0.059 Uiso 1 1 calc R U . . .
C9 C -0.0198(2) 0.24376(12) 0.40923(12) 0.0482(3) Uani 1 1 d . . . . .
H9A H -0.006374 0.156876 0.359323 0.058 Uiso 1 1 calc R U . . .
H9B H -0.177852 0.261128 0.450928 0.058 Uiso 1 1 calc R U . . .
C10 C -0.2009(2) 0.45378(14) 0.29862(12) 0.0517(3) Uani 1 1 d . . . . .
H10A H -0.328802 0.398251 0.292161 0.062 Uiso 1 1 calc R U . . .
H10B H -0.181434 0.501977 0.215405 0.062 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.3119(14) . ?
N1 C2 1.3466(13) . ?
F1 C3 1.3647(11) . ?
N2 C2 1.3580(14) . ?
F2 C5 1.3556(12) . ?
C2 C3 1.3854(15) . ?
N3 C4 1.3572(15) . ?
F3 C6 1.3494(12) . ?
C3 C4 1.3856(15) . ?
C4 C5 1.3969(15) . ?
C5 C6 1.3578(16) . ?
O1 C7 1.4197(13) . ?
O1 C8 1.4280(13) . ?
O2 C10 1.4241(16) . ?
O2 C9 1.4321(14) . ?
C7 C10 1.5017(17) 2_566 ?
C8 C9 1.4919(18) . ?

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 N1 C2 116.73(10) . . ?
N1 C2 N2 118.02(10) . . ?
N1 C2 C3 120.07(10) . . ?
N2 C2 C3 121.92(10) . . ?
F1 C3 C2 118.47(9) . . ?
F1 C3 C4 118.17(10) . . ?
C2 C3 C4 123.37(10) . . ?
N3 C4 C3 123.29(10) . . ?
N3 C4 C5 122.42(10) . . ?
C3 C4 C5 114.25(10) . . ?
C6 C5 F2 121.70(10) . . ?
C6 C5 C4 119.26(10) . . ?
F2 C5 C4 119.03(10) . . ?
N1 C6 C5 126.31(10) . . ?
N1 C6 F3 115.40(10) . . ?
C5 C6 F3 118.30(10) . . ?
C7 O1 C8 114.01(9) . . ?
C10 O2 C9 114.08(9) . . ?
O1 C7 C10 109.30(10) . 2_566 ?
O1 C8 C9 111.89(10) . . ?
O2 C9 C8 111.51(10) . . ?
O2 C10 C7 113.03(10) . 2_566 ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037


