Co-crystals of polyhalogenated diaminobenzonitriles with 18-crown-6: effect of fluorine on the stoichiometry and supramolecular structure
Vaganova, Tamara A.; Gatilov, Yurij V.; Malykhin, Sergey E.; Pishchur, Denis P.; Sukhov, Maxim; Zakharov, Boris A.; Boldyreva, Elena V.; Malykhin, Evgenij V.; CrystEngComm 23 (2021) 4767–4781; doi:10.1039/D1CE00530H

data_7242975
_publ_section_title
;
 Co-crystals of polyhalogenated diaminobenzonitriles with 18-crown-6:
 effect of fluorine on the stoichiometry and supramolecular structure
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              4767
_journal_page_last               4781
_journal_paper_doi               10.1039/D1CE00530H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         '3(C12 H24 O6), 4(C7 H4 F3 N3)'
_chemical_formula_sum            'C64 H88 F12 N12 O18'
_chemical_formula_weight         1541.46
_chemical_melting_point          393
_chemical_name_common
;
2,4-diamino-3,5,6-trifluorobenzonitrile--18-crown-6 ether (4:3)
;
_chemical_name_systematic
;
2,4-diamino-3,5,6-trifluorobenzonitrile--18-crown-6 ether (4:3)
;
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-02 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                113.393(7)
_cell_angle_beta                 98.517(5)
_cell_angle_gamma                103.527(6)
_cell_formula_units_Z            1
_cell_length_a                   11.7416(7)
_cell_length_b                   12.0658(10)
_cell_length_c                   15.0919(10)
_cell_measurement_reflns_used    3011
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.6530
_cell_measurement_theta_min      4.4570
_cell_volume                     1837.0(3)
_computing_cell_refinement
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)'
_computing_data_collection
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10728
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.853
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.144
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         6512
_refine_ls_number_restraints     198
_refine_ls_restrained_S_all      0.836
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0392
_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/[\s^2^(Fo^2^)+(0.0433P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3576
_reflns_number_total             6512
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00530h2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7242975--7242982.cif.'
_cod_original_cell_volume        1837.0(2)
_cod_database_code               7242975
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              1714