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_7242980
_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         'C12 H24 O6, C7 H5 Cl F N3'
_chemical_formula_sum            'C19 H29 Cl F N3 O6'
_chemical_formula_weight         449.90
_chemical_melting_point          414
_chemical_name_systematic
;
2,6-diamino-4-chloro-3-fluorobenzonitrile and 18-crown-6, 1:1 co-crystal
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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
;
2021-04-08 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.123(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.0089(13)
_cell_length_b                   10.1240(5)
_cell_length_c                   17.2092(7)
_cell_measurement_reflns_used    6073
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      22.21
_cell_measurement_theta_min      2.39
_cell_volume                     4669.3(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    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0506
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26879
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.113
_diffrn_reflns_theta_max         25.113
_diffrn_reflns_theta_min         2.150
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9118
_exptl_absorpt_correction_T_min  0.8001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4146
_refine_ls_number_restraints     196
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0815
_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^)+(0.1748P)^2^+6.8591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2553
_refine_ls_wR_factor_ref         0.2998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2649
_reflns_number_total             4146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00530h2.cif
_cod_data_source_block           Ecr-c_5mal
_cod_depositor_comments
'Adding full bibliography for 7242975--7242982.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7242980
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.881
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              52374