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
Vaganova, Tamara; Gatilov, Yurij; Kryuchkova, Natalia; Pishchur, Denis; Malykhin, Evgenij; CrystEngComm 26 (2024) 4602–4616; doi:10.1039/D4CE00612G

data_7249099
_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(C6 H4 F3 N3 O2), C8 H16 O4'
_chemical_formula_sum            'C20 H24 F6 N6 O8'
_chemical_formula_weight         590.45
_chemical_melting_point          403
_chemical_name_systematic
;
Co-crystal of 2,4-diaminotrifluoronitrobenzene and 12-crown-4, 2:1
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 90.584(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4617(18)
_cell_length_b                   21.673(3)
_cell_length_c                   7.3234(8)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.77
_cell_measurement_theta_min      2.63
_cell_volume                     2454.0(5)
_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 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.1265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            43266
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.219
_diffrn_reflns_theta_min         1.317
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.8028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       prismoid
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.363
_refine_ls_R_factor_all          0.1992
_refine_ls_R_factor_gt           0.1404
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4282
_refine_ls_wR_factor_ref         0.4467
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2325
_reflns_number_total             4876
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00612g2.cif
_cod_data_source_block           t7021_4_2C12cr4
_cod_depositor_comments
'Adding full bibliography for 7249096--7249100.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249099
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              87155
_shelx_hkl_checksum              52520