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#$Date: 2024-09-06 03:20:09 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294531 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/91/7249100.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249100
loop_
_publ_author_name
'Vaganova, Tamara'
'Gatilov, Yurij'
'Kryuchkova, Natalia'
'Pishchur, Denis'
'Malykhin, Evgenij'
_publ_section_title
;
 Competition of intermolecular interactions in the self-assembly of
 co-crystals of trifluoro-meta-arylenediamines (benzene, nitrobenzene,
 pyridine) with 12-, 15-, and 18-membered crown ethers
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              4602
_journal_page_last               4616
_journal_paper_doi               10.1039/D4CE00612G
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '2(C5 H4 F3 N3), C8 H16 O4'
_chemical_formula_sum            'C18 H24 F6 N6 O4'
_chemical_formula_weight         502.43
_chemical_melting_point          351
_chemical_name_systematic
;
Co-crystal of 2,4-diaminotrifluoropyridine and 12-crown-4, 2:1
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-06-14 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                88.963(2)
_cell_angle_beta                 87.032(2)
_cell_angle_gamma                81.176(2)
_cell_formula_units_Z            1
_cell_length_a                   5.7104(2)
_cell_length_b                   9.5020(4)
_cell_length_c                   10.2481(5)
_cell_measurement_reflns_used    8454
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.17
_cell_measurement_theta_min      2.17
_cell_volume                     548.72(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19664
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.171
_diffrn_reflns_theta_min         2.929
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.9323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0492P)²+0.0857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2344
_reflns_number_total             2944
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00612g2.cif
_cod_data_source_block           m403_2B12cr4
_cod_depositor_comments
'Adding full bibliography for 7249096--7249100.cif.'
_cod_database_code               7249100
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 . . .
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'
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 ?
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) . ?
