#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:38:55 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/34/7233428.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_7233428
loop_
_publ_author_name
'Vaganova, Tamara A.'
'Gatilov, Yurij V.'
'Benassi, Enrico'
'Chuikov, Igor P.'
'Pishchur, Denis P.'
'Malykhin, Evgenij V.'
_publ_section_title
;
 Impact of molecular packing rearrangement on solid-state fluorescence:
 polyhalogenated N-hetarylamines vs. their co-crystals with 18-crown-6
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              5931
_journal_paper_doi               10.1039/C9CE00645A
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         '2(C5 H2 Cl5 F5 N5), C12 H24 O6'
_chemical_formula_sum            'C22 H28 Cl4 F4 N4 O6'
_chemical_formula_weight         662.28
_chemical_melting_point          372
_chemical_name_systematic
;
4-amino-3,5-dichloro-2,6-difluoropyridine 18-crown-6, associate 2:1
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-22 deposited with the CCDC.    2019-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.630(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2435(8)
_cell_length_b                   9.9058(4)
_cell_length_c                   17.6406(8)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.39
_cell_volume                     2923.0(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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0509
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.207
_diffrn_reflns_theta_min         2.390
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         4345
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0474
_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)+(0.0533P)²+2.9450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3147
_reflns_number_total             4345
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00645a2.cif
_cod_data_source_block           2Cxcr-M11_a
_cod_depositor_comments
'Adding full bibliography for 7233421--7233432.cif.'
_cod_database_code               7233428
_shelx_shelxl_version_number     2014/7
_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   0.867
_shelx_estimated_absorpt_t_max   0.937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cl1 Cl 0.28917(4) 0.58667(6) 0.03284(4) 0.07046(19) Uani 1 1 d . .
F1 F 0.19702(8) 0.41735(17) 0.08608(10) 0.0808(4) Uani 1 1 d . .
N1 N 0.27610(10) 0.2352(2) 0.13023(12) 0.0608(4) Uani 1 1 d . .
C1 C 0.26413(11) 0.3563(2) 0.09734(13) 0.0547(5) Uani 1 1 d . .
O1 O 0.62503(8) 0.53290(16) 0.68530(9) 0.0577(3) Uani 1 1 d . .
Cl2 Cl 0.47901(4) 0.14276(6) 0.13751(5) 0.07258(19) Uani 1 1 d . .
N2 N 0.43334(11) 0.42321(18) 0.06508(14) 0.0579(4) Uani 1 1 d D .
H2A H 0.4788(11) 0.387(2) 0.0785(16) 0.065(7) Uiso 1 1 d D .
H2B H 0.4277(16) 0.5077(18) 0.0522(17) 0.076(8) Uiso 1 1 d D .
F2 F 0.35477(10) 0.05184(15) 0.17456(11) 0.0857(5) Uani 1 1 d . .
O2 O 0.58023(7) 0.69962(14) 0.53975(9) 0.0523(3) Uani 1 1 d . .
C2 C 0.31281(10) 0.42603(19) 0.07478(12) 0.0465(4) Uani 1 1 d . .
O3 O 0.48613(9) 0.69179(15) 0.35609(10) 0.0617(4) Uani 1 1 d . .
C3 C 0.38347(10) 0.36343(18) 0.08678(11) 0.0426(4) Uani 1 1 d . .
C4 C 0.39592(11) 0.23174(19) 0.12089(12) 0.0474(4) Uani 1 1 d . .
C5 C 0.34144(13) 0.1768(2) 0.14088(14) 0.0563(5) Uani 1 1 d . .
C6 C 0.68113(11) 0.5890(2) 0.66429(14) 0.0585(5) Uani 1 1 d . .
H6A H 0.6893 0.5275 0.6266 0.070 Uiso 1 1 calc R U
H6B H 0.7320 0.6016 0.7172 0.070 Uiso 1 1 calc R U
C7 C 0.65186(11) 0.7198(2) 0.61987(14) 0.0583(5) Uani 1 1 d . .
H7A H 0.6419 0.7804 0.6567 0.070 Uiso 1 1 calc R U
H7B H 0.6920 0.7605 0.6091 0.070 Uiso 1 1 calc R U
C8 C 0.55691(14) 0.8175(2) 0.48607(16) 0.0611(5) Uani 1 1 d . .
H8A H 0.5960 0.8374 0.4681 0.073 Uiso 1 1 calc R U
H8B H 0.5539 0.8943 0.5184 0.073 Uiso 1 1 calc R U
C9 C 0.47686(13) 0.7921(2) 0.40764(16) 0.0635(5) Uani 1 1 d . .
H9A H 0.4393 0.7616 0.4256 0.076 Uiso 1 1 calc R U
H9B H 0.4564 0.8746 0.3742 0.076 Uiso 1 1 calc R U
C10 C 0.41623(15) 0.6654(3) 0.27312(15) 0.0705(6) Uani 1 1 d . .
H10A H 0.4313 0.6087 0.2388 0.085 Uiso 1 1 calc R U
H10B H 0.3966 0.7501 0.2422 0.085 Uiso 1 1 calc R U
C11 C 0.35099(13) 0.5990(3) 0.27996(15) 0.0653(6) Uani 1 1 d . .
H11A H 0.3378 0.6515 0.3176 0.078 Uiso 1 1 calc R U
H11B H 0.3037 0.5937 0.2228 0.078 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
C1 N1 C5 114.59(17) .
N1 C1 F1 115.10(17) .
N1 C1 C2 126.70(18) .
F1 C1 C2 118.2(2) .
C11 O1 C6 110.28(16) 5_666
C3 N2 H2A 121.0(17) .
C3 N2 H2B 119.5(18) .
H2A N2 H2B 117(2) .
C7 O2 C8 112.18(16) .
C1 C2 C3 118.70(18) .
C1 C2 Cl1 121.20(15) .
C3 C2 Cl1 120.10(14) .
C9 O3 C10 115.41(18) .
N2 C3 C4 122.65(16) .
N2 C3 C2 122.54(17) .
C4 C3 C2 114.78(16) .
C5 C4 C3 119.14(17) .
C5 C4 Cl2 121.14(16) .
C3 C4 Cl2 119.72(13) .
N1 C5 F2 115.50(18) .
N1 C5 C4 126.1(2) .
F2 C5 C4 118.4(2) .
O1 C6 C7 110.07(16) .
O1 C6 H6A 109.6 .
C7 C6 H6A 109.6 .
O1 C6 H6B 109.6 .
C7 C6 H6B 109.6 .
H6A C6 H6B 108.2 .
O2 C7 C6 109.49(16) .
O2 C7 H7A 109.8 .
C6 C7 H7A 109.8 .
O2 C7 H7B 109.8 .
C6 C7 H7B 109.8 .
H7A C7 H7B 108.2 .
O2 C8 C9 108.49(16) .
O2 C8 H8A 110.0 .
C9 C8 H8A 110.0 .
O2 C8 H8B 110.0 .
C9 C8 H8B 110.0 .
H8A C8 H8B 108.4 .
O3 C9 C8 108.22(18) .
O3 C9 H9A 110.1 .
C8 C9 H9A 110.1 .
O3 C9 H9B 110.1 .
C8 C9 H9B 110.1 .
H9A C9 H9B 108.4 .
O3 C10 C11 113.78(19) .
O3 C10 H10A 108.8 .
C11 C10 H10A 108.8 .
O3 C10 H10B 108.8 .
C11 C10 H10B 108.8 .
H10A C10 H10B 107.7 .
O1 C11 C10 109.75(19) 5_666
O1 C11 H11A 109.7 5_666
C10 C11 H11A 109.7 .
O1 C11 H11B 109.7 5_666
C10 C11 H11B 109.7 .
H11A C11 H11B 108.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.719(2) .
F1 C1 1.349(2) .
N1 C1 1.302(3) .
N1 C5 1.311(3) .
C1 C2 1.372(3) .
O1 C11 1.420(3) 5_666
O1 C6 1.417(2) .
Cl2 C4 1.7193(19) .
N2 C3 1.335(2) .
N2 H2A 0.863(16) .
N2 H2B 0.860(17) .
F2 C5 1.342(3) .
O2 C7 1.418(2) .
O2 C8 1.429(3) .
C2 C3 1.412(2) .
O3 C9 1.416(3) .
O3 C10 1.440(3) .
C3 C4 1.407(3) .
C4 C5 1.373(3) .
C6 C7 1.474(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.498(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.474(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 O1 1.420(3) 5_666
C11 H11A 0.9700 .
C11 H11B 0.9700 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C5 N1 C1 F1 179.99(18) . .
C5 N1 C1 C2 -0.9(3) . .
N1 C1 C2 C3 0.5(3) . .
F1 C1 C2 C3 179.61(17) . .
N1 C1 C2 Cl1 -179.34(17) . .
F1 C1 C2 Cl1 -0.3(3) . .
C1 C2 C3 N2 178.75(19) . .
Cl1 C2 C3 N2 -1.4(3) . .
C1 C2 C3 C4 0.6(3) . .
Cl1 C2 C3 C4 -179.53(13) . .
N2 C3 C4 C5 -179.41(19) . .
C2 C3 C4 C5 -1.2(3) . .
N2 C3 C4 Cl2 1.0(3) . .
C2 C3 C4 Cl2 179.17(14) . .
C1 N1 C5 F2 -179.86(18) . .
C1 N1 C5 C4 0.1(3) . .
C3 C4 C5 N1 1.0(3) . .
Cl2 C4 C5 N1 -179.46(17) . .
C3 C4 C5 F2 -179.04(17) . .
Cl2 C4 C5 F2 0.5(3) . .
C11 O1 C6 C7 174.13(17) 5_666 .
C8 O2 C7 C6 -168.97(17) . .
O1 C6 C7 O2 -63.2(2) . .
C7 O2 C8 C9 -174.13(18) . .
C10 O3 C9 C8 -173.63(18) . .
O2 C8 C9 O3 -67.5(2) . .
C9 O3 C10 C11 -69.1(3) . .
O3 C10 C11 O1 -66.1(3) . 5_666
