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_7244180
_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         'C7 H3 F3 N2'
_chemical_formula_sum            'C7 H3 F3 N2'
_chemical_formula_weight         172.11
_chemical_melting_point          369
_chemical_name_systematic        4-amino-2,3,5-trifluorobenzonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                90
_cell_angle_beta                 96.061(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.7360(7)
_cell_length_b                   8.4997(17)
_cell_length_c                   10.654(2)
_cell_measurement_reflns_used    1346
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      3.07
_cell_volume                     336.43(11)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2291
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.828
_diffrn_reflns_theta_min         3.073
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_correction_T_min  0.8193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       prism
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.815
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1092
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.813
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0977P)^2^+0.0066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_full    0.713
_reflns_Friedel_fraction_max     0.674
_reflns_number_gt                990
_reflns_number_total             1092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01469b2.cif
_cod_data_source_block           C-M96
_cod_depositor_comments
'Adding full bibliography for 7244175--7244182.cif.'
_cod_original_cell_volume        336.44(12)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7244180
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              25781
_shelx_hkl_checksum              98642