Polyhalogenated aminobenzonitriles vs. their co-crystals with 18-crown-6: amino group position as a tool to control crystal packing and solid-state fluorescence
Vaganova, Tamara A.; Benassi, Enrico; Gatilov, Yurij V.; Chuikov, Igor P.; Pishchur, Denis P.; Malykhin, Evgenij V.; CrystEngComm 24 (2022) 987–1001; doi:10.1039/D1CE01469B

data_7244182
_publ_section_title
;
 Polyhalogenated aminobenzonitriles vs. their co-crystals with 18-crown-6:
 amino group position as a tool to control crystal packing and solid-state
 fluorescence
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              987
_journal_page_last               1001
_journal_paper_doi               10.1039/D1CE01469B
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         '2(C7 H2 Cl F3 N1), C12 H24 O6'
_chemical_formula_sum            'C26 H28 Cl2 F6 N4 O6'
_chemical_formula_weight         677.42
_chemical_melting_point          371
_chemical_name_systematic
;
2-amino-4-chloro-3,5,6-trifluorobenzonitrile 18-crown-6 associate 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
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                111.749(2)
_cell_angle_beta                 97.219(3)
_cell_angle_gamma                116.798(2)
_cell_formula_units_Z            1
_cell_length_a                   9.4276(6)
_cell_length_b                   9.9092(6)
_cell_length_c                   10.3213(7)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.27
_cell_volume                     747.91(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0226
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20110
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.910
_diffrn_reflns_theta_min         2.271
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.8372
_exptl_absorpt_correction_T_min  0.8058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0434P)^2^+0.2376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3092
_reflns_number_total             3585
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01469b2.cif
_cod_data_source_block           2Dcr-M25
_cod_depositor_comments
'Adding full bibliography for 7244175--7244182.cif.'
_cod_original_cell_volume        747.91(8)
_cod_database_code               7244182
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.847
_shelx_estimated_absorpt_t_max   0.912
_shelx_res_checksum              62333
_shelx_hkl_checksum              40281