#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:19:41 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272610 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/41/7244181.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_7244181
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 H3 Cl F2 N2), C12 H24 O6'
_chemical_formula_sum            'C26 H30 Cl2 F4 N4 O6'
_chemical_formula_weight         641.44
_chemical_melting_point          390
_chemical_name_systematic
;
2-amino-4-chloro-3,6-difluorobenzonitrile 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                111.106(2)
_cell_angle_beta                 98.506(2)
_cell_angle_gamma                116.108(2)
_cell_formula_units_Z            1
_cell_length_a                   9.2760(4)
_cell_length_b                   9.8840(5)
_cell_length_c                   10.2679(5)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.28
_cell_volume                     734.00(7)
_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 0.996
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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            20065
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.043
_diffrn_reflns_theta_min         2.517
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.8372
_exptl_absorpt_correction_T_min  0.7724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3547
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0370
_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/[σ²(Fo²)+(0.0555P)²+0.2075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3009
_reflns_number_total             3547
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01469b2.cif
_cod_data_source_block           2Ecr-M26
_cod_depositor_comments
'Adding full bibliography for 7244175--7244182.cif.'
_cod_original_cell_volume        734.00(6)
_cod_database_code               7244181
_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   0.848
_shelx_estimated_absorpt_t_max   0.955
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 1.33654(5) 0.60055(5) 0.42854(5) 0.05965(15) Uani 1 1 d . . . . .
N2 N 0.6208(2) -0.0920(2) 0.4135(2) 0.0770(5) Uani 1 1 d . . . . .
C1 C 0.87780(17) 0.15968(17) 0.41556(15) 0.0400(3) Uani 1 1 d . . . . .
F1 F 0.98429(12) 0.40978(11) 0.22124(10) 0.0542(2) Uani 1 1 d . . . . .
N1 N 0.69962(15) 0.14211(16) 0.20337(14) 0.0425(3) Uani 1 1 d D . . . .
H1 H 0.623(2) 0.0389(19) 0.183(2) 0.054(5) Uiso 1 1 d D . . . .
H2 H 0.701(2) 0.158(2) 0.1261(18) 0.053(5) Uiso 1 1 d D . . . .
C2 C 0.85499(16) 0.21379(15) 0.30886(14) 0.0341(3) Uani 1 1 d . . . . .
F2 F 1.05591(15) 0.18896(17) 0.62423(13) 0.0795(4) Uani 1 1 d . . . . .
C3 C 1.00314(17) 0.35424(16) 0.32120(14) 0.0368(3) Uani 1 1 d . . . . .
C4 C 1.16244(18) 0.43288(17) 0.42691(16) 0.0422(3) Uani 1 1 d . . . . .
C5 C 1.18489(19) 0.3775(2) 0.53079(17) 0.0525(4) Uani 1 1 d . . . . .
H5 H 1.292802 0.429259 0.602381 0.063 Uiso 1 1 calc R U . . .
C6 C 1.0412(2) 0.2436(2) 0.52309(17) 0.0499(4) Uani 1 1 d . . . . .
C7 C 0.7345(2) 0.0193(2) 0.41426(17) 0.0505(4) Uani 1 1 d . . . . .
O1 O 0.21918(15) 1.00687(14) 0.08684(12) 0.0499(3) Uani 1 1 d . . . . .
O2 O 0.34646(12) 0.79803(12) 0.07440(12) 0.0435(2) Uani 1 1 d . . . . .
O3 O 0.63372(15) 0.77301(15) 0.04699(14) 0.0571(3) Uani 1 1 d . . . . .
C8 C 0.2383(3) 1.1691(3) 0.1350(3) 0.0723(6) Uani 1 1 d . . . . .
H8A H 0.347027 1.256006 0.218393 0.087 Uiso 1 1 calc R U . . .
H8B H 0.146061 1.167686 0.169576 0.087 Uiso 1 1 calc R U . . .
C9 C 0.2556(2) 0.9765(2) 0.20895(18) 0.0539(4) Uani 1 1 d . . . . .
H9A H 0.179264 0.982719 0.262821 0.065 Uiso 1 1 calc R U . . .
H9B H 0.373567 1.063012 0.277807 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2303(2) 0.8030(2) 0.15001(19) 0.0521(4) Uani 1 1 d . . . . .
H10A H 0.252081 0.779096 0.232041 0.063 Uiso 1 1 calc R U . . .
H10B H 0.112340 0.716448 0.081137 0.063 Uiso 1 1 calc R U . . .
C11 C 0.3428(2) 0.64199(19) 0.0279(2) 0.0544(4) Uani 1 1 d . . . . .
H11A H 0.226770 0.545070 -0.037036 0.065 Uiso 1 1 calc R U . . .
H11B H 0.377994 0.629644 0.114621 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4648(2) 0.6468(2) -0.05506(19) 0.0571(4) Uani 1 1 d . . . . .
H12A H 0.452709 0.535890 -0.100275 0.068 Uiso 1 1 calc R U . . .
H12B H 0.438142 0.673356 -0.134209 0.068 Uiso 1 1 calc R U . . .
C13 C 0.7661(3) 0.7867(3) -0.0111(3) 0.0734(6) Uani 1 1 d . . . . .
H13A H 0.759721 0.678299 -0.046846 0.088 Uiso 1 1 calc R U . . .
H13B H 0.876533 0.873434 0.070299 0.088 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 119.64(12) . . ?
C6 C1 C7 119.88(13) . . ?
C2 C1 C7 120.48(12) . . ?
N1 C2 C3 120.65(12) . . ?
N1 C2 C1 123.25(12) . . ?
C3 C2 C1 116.04(12) . . ?
F1 C3 C4 119.78(12) . . ?
F1 C3 C2 117.18(12) . . ?
C4 C3 C2 123.02(12) . . ?
C3 C4 C5 120.75(13) . . ?
C3 C4 Cl1 119.10(11) . . ?
C5 C4 Cl1 120.14(11) . . ?
C6 C5 C4 117.12(13) . . ?
F2 C6 C5 119.19(14) . . ?
F2 C6 C1 117.42(13) . . ?
C5 C6 C1 123.39(14) . . ?
N2 C7 C1 179.87(15) . . ?
C8 O1 C9 111.82(14) . . ?
C11 O2 C10 112.36(12) . . ?
C12 O3 C13 115.83(15) . . ?
O1 C8 C13 110.96(16) . 2_675 ?
O1 C9 C10 108.88(13) . . ?
O2 C10 C9 108.93(12) . . ?
O2 C11 C12 108.26(12) . . ?
O3 C12 C11 108.56(14) . . ?
O3 C13 C8 115.81(17) . 2_675 ?
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 1.7237(14) . ?
N2 C7 1.137(2) . ?
C1 C6 1.394(2) . ?
C1 C2 1.4086(18) . ?
C1 C7 1.4318(19) . ?
F1 C3 1.3500(15) . ?
N1 C2 1.3562(18) . ?
C2 C3 1.4051(17) . ?
F2 C6 1.3475(17) . ?
C3 C4 1.369(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.369(2) . ?
O1 C8 1.414(2) . ?
O1 C9 1.4184(19) . ?
O2 C11 1.4235(18) . ?
O2 C10 1.4256(18) . ?
O3 C12 1.401(2) . ?
O3 C13 1.418(2) . ?
C8 C13 1.486(3) 2_675 ?
C9 C10 1.489(2) . ?
C11 C12 1.509(3) . ?
