#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:19:41 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272610 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/41/7244182.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7244182
loop_
_publ_author_name
'Vaganova, Tamara A.'
'Benassi, Enrico'
'Gatilov, Yurij V.'
'Chuikov, Igor P.'
'Pishchur, Denis P.'
'Malykhin, Evgenij V.'
_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       'φ and ω 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/[σ²(Fo²)+(0.0434P)²+0.2376P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.847
_shelx_estimated_absorpt_t_max   0.912
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.32845(5) 1.10514(5) 0.91563(5) 0.05709(13) Uani 1 1 d . . . . .
F1 F 0.97746(12) 0.91796(11) 0.71854(10) 0.0546(2) Uani 1 1 d . . . . .
N2 N 0.6214(2) 0.4197(2) 0.91805(19) 0.0726(5) Uani 1 1 d . . . . .
C1 C 0.87468(17) 0.66494(17) 0.90902(15) 0.0393(3) Uani 1 1 d . . . . .
N1 N 0.69626(15) 0.65159(16) 0.70624(14) 0.0438(3) Uani 1 1 d D . . . .
H1 H 0.696(2) 0.662(2) 0.6277(18) 0.061(5) Uiso 1 1 d D . . . .
H2 H 0.618(2) 0.5465(19) 0.684(2) 0.058(5) Uiso 1 1 d D . . . .
C2 C 0.85112(16) 0.72031(16) 0.80531(14) 0.0348(3) Uani 1 1 d . . . . .
F2 F 1.33036(12) 0.94773(15) 1.10767(12) 0.0738(3) Uani 1 1 d . . . . .
C3 C 0.99694(17) 0.85961(16) 0.81441(14) 0.0368(3) Uani 1 1 d . . . . .
F3 F 1.05473(14) 0.69072(15) 1.10944(12) 0.0736(3) Uani 1 1 d . . . . .
C4 C 1.15590(17) 0.93736(17) 0.91361(15) 0.0402(3) Uani 1 1 d . . . . .
C5 C 1.17574(18) 0.87752(19) 1.01202(16) 0.0466(3) Uani 1 1 d . . . . .
C6 C 1.0361(2) 0.7448(2) 1.01056(16) 0.0467(3) Uani 1 1 d . . . . .
C7 C 0.7329(2) 0.5272(2) 0.91278(16) 0.0488(3) Uani 1 1 d . . . . .
O1 O 0.21661(14) 0.50658(14) 0.58331(12) 0.0507(3) Uani 1 1 d . . . . .
O2 O 0.35095(12) 0.30662(12) 0.57997(11) 0.0445(2) Uani 1 1 d . . . . .
O3 O 0.63829(15) 0.28477(15) 0.56010(13) 0.0558(3) Uani 1 1 d . . . . .
C8 C 0.2349(3) 0.6686(2) 0.6263(2) 0.0687(5) Uani 1 1 d . . . . .
H8A H 0.341812 0.758737 0.707880 0.082 Uiso 1 1 calc R U . . .
H8B H 0.143751 0.668561 0.660699 0.082 Uiso 1 1 calc R U . . .
C9 C 0.2550(2) 0.4829(2) 0.70733(18) 0.0552(4) Uani 1 1 d . . . . .
H9A H 0.179546 0.489670 0.761734 0.066 Uiso 1 1 calc R U . . .
H9B H 0.370828 0.573175 0.774093 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2340(2) 0.3111(2) 0.65400(19) 0.0534(4) Uani 1 1 d . . . . .
H10A H 0.255475 0.291677 0.737822 0.064 Uiso 1 1 calc R U . . .
H10B H 0.118737 0.220849 0.585928 0.064 Uiso 1 1 calc R U . . .
C11 C 0.3492(2) 0.15180(19) 0.53748(19) 0.0519(4) Uani 1 1 d . . . . .
H11A H 0.235832 0.052642 0.472900 0.062 Uiso 1 1 calc R U . . .
H11B H 0.382041 0.142456 0.625162 0.062 Uiso 1 1 calc R U . . .
C12 C 0.4716(2) 0.1561(2) 0.45713(18) 0.0544(4) Uani 1 1 d . . . . .
H12A H 0.459481 0.044609 0.413204 0.065 Uiso 1 1 calc R U . . .
H12B H 0.448300 0.181579 0.377786 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7696(3) 0.2955(3) 0.5024(3) 0.0700(5) Uani 1 1 d . . . . .
H13A H 0.763928 0.187470 0.471273 0.084 Uiso 1 1 calc R U . . .
H13B H 0.877945 0.385767 0.582218 0.084 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.28(12) . . ?
C6 C1 C7 119.14(13) . . ?
C2 C1 C7 120.57(12) . . ?
N1 C2 C3 120.63(12) . . ?
N1 C2 C1 123.26(12) . . ?
C3 C2 C1 116.02(12) . . ?
F1 C3 C4 119.02(12) . . ?
F1 C3 C2 117.30(12) . . ?
C4 C3 C2 123.68(12) . . ?
C3 C4 C5 118.98(12) . . ?
C3 C4 Cl1 120.79(11) . . ?
C5 C4 Cl1 120.24(11) . . ?
F2 C5 C6 120.01(14) . . ?
F2 C5 C4 120.40(13) . . ?
C6 C5 C4 119.59(13) . . ?
F3 C6 C5 119.53(13) . . ?
F3 C6 C1 119.05(13) . . ?
C5 C6 C1 121.41(13) . . ?
N2 C7 C1 178.95(18) . . ?
C8 O1 C9 112.27(13) . . ?
C11 O2 C10 112.16(11) . . ?
C12 O3 C13 115.20(14) . . ?
O1 C8 C13 110.44(15) . 2_666 ?
O1 C9 C10 109.28(13) . . ?
O2 C10 C9 108.89(12) . . ?
O2 C11 C12 108.48(12) . . ?
O3 C12 C11 108.68(13) . . ?
O3 C13 C8 115.49(16) . 2_666 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.7141(14) . ?
F1 C3 1.3496(15) . ?
N2 C7 1.136(2) . ?
C1 C6 1.393(2) . ?
C1 C2 1.4077(18) . ?
C1 C7 1.4346(19) . ?
N1 C2 1.3612(18) . ?
C2 C3 1.4016(18) . ?
F2 C5 1.3411(17) . ?
C3 C4 1.3698(19) . ?
F3 C6 1.3431(17) . ?
C4 C5 1.384(2) . ?
C5 C6 1.372(2) . ?
O1 C8 1.417(2) . ?
O1 C9 1.4165(19) . ?
O2 C11 1.4224(18) . ?
O2 C10 1.4252(18) . ?
O3 C12 1.412(2) . ?
O3 C13 1.418(2) . ?
C8 C13 1.498(3) 2_666 ?
C9 C10 1.489(2) . ?
C11 C12 1.498(2) . ?
