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_7244177
_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 H2 Cl F3 N2'
_chemical_formula_sum            'C7 H2 Cl F3 N2'
_chemical_formula_weight         206.56
_chemical_melting_point          396
_chemical_name_systematic        2-amino-4-chloro-3,5,6-trifluorobenzonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 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
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.955(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7777(19)
_cell_length_b                   7.7816(15)
_cell_length_c                   10.2460(16)
_cell_measurement_reflns_used    2405
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      3.37
_cell_volume                     767.8(2)
_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 0.976
_diffrn_measured_fraction_theta_max 0.971
_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  0.0230
_diffrn_reflns_av_unetI/netI     0.1039
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3105
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.145
_diffrn_reflns_theta_min         3.366
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  0.6938
_exptl_absorpt_correction_T_min  0.5694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0962
_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^)+(0.0039P)^2^+14.9187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2726
_refine_ls_wR_factor_ref         0.2820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                505
_reflns_number_total             799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01469b2.cif
_cod_data_source_block           D-Mal1275
_cod_depositor_comments
'Adding full bibliography for 7244175--7244182.cif.'
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7244177
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.735
_shelx_estimated_absorpt_t_max   0.834
_shelx_res_checksum              88322
_shelx_hkl_checksum              46050