#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:05:25 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229007 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/98/7229856.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_7229856
loop_
_publ_author_name
'Vaganova, Tamara A.'
'Gatilov, Yurij V.'
'Pishchur, Denis P.'
'Chuikov, Igor P.'
'Malykhin, Evgenij V.'
_publ_section_title
;
 Controlled self-assembly of π-stacked/H-bonded 1D crystal structures
 from polyfluorinated arylamines and 18-crown-6 (2 : 1).
 Associatevs.co-former fluorescence properties
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              807
_journal_paper_doi               10.1039/C7CE01851G
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         '2(C5 H2 F4 N2), C12 H24 O6'
_chemical_formula_sum            'C22 H28 F8 N4 O6'
_chemical_formula_weight         596.48
_chemical_melting_point          403
_chemical_name_systematic
; 
 4-amino-2,3,5,6-tetrafluoropyridine and 18-crown-6 2:1 associate
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-10-19 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.4540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.5893(6)
_cell_length_b                   9.6007(3)
_cell_length_c                   16.5096(5)
_cell_measurement_reflns_used    8123
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      2.45
_cell_volume                     2637.95(14)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24923
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_correction_T_min  0.8908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0491P)²+4.1527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                2345
_reflns_number_total             3041
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce01851g2.cif
_cod_data_source_block           2Fcr-m914
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7229852--7229857.cif.
;
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               7229856
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.91222(9) 0.28910(16) -0.03473(11) 0.0479(4) Uani 1 1 d . . .
O2 O 1.01436(11) 0.30480(19) 0.14764(13) 0.0694(6) Uani 1 1 d D . .
O3 O 1.12418(10) 0.54377(17) 0.18561(11) 0.0532(4) Uani 1 1 d D . .
C6 C 0.9336(2) 0.1692(3) 0.0239(2) 0.0654(8) Uani 1 1 d . . .
H6A H 0.9322 0.0844 -0.0109 0.078 Uiso 1 1 calc R B .
H6B H 0.8943 0.1572 0.0488 0.078 Uiso 1 1 calc R . .
C7 C 1.0147(2) 0.1880(3) 0.0985(2) 0.0754(9) Uani 1 1 d D B .
H7A H 1.0302 0.1049 0.1381 0.090 Uiso 1 1 calc R A 2
H7B H 1.0541 0.2002 0.0739 0.090 Uiso 1 1 calc R A 2
C8 C 1.0842(2) 0.3428(4) 0.2337(2) 0.0472(12) Uani 0.672(8) 1 d PD B 1
H8A H 1.1052 0.2585 0.2716 0.057 Uiso 0.672(8) 1 calc PR B 1
H8B H 1.0672 0.4098 0.2674 0.057 Uiso 0.672(8) 1 calc PR B 1
C9 C 1.1486(2) 0.4062(4) 0.2155(3) 0.0459(11) Uani 0.672(8) 1 d PD B 1
H9A H 1.2002 0.4067 0.2713 0.055 Uiso 0.672(8) 1 calc PR B 1
H9B H 1.1559 0.3525 0.1685 0.055 Uiso 0.672(8) 1 calc PR B 1
C8A C 1.1040(5) 0.2915(9) 0.1939(6) 0.062(3) Uani 0.328(8) 1 d PD B 2
H8A1 H 1.1220 0.2098 0.2347 0.075 Uiso 0.328(8) 1 calc PR B 2
H8A2 H 1.1271 0.2873 0.1503 0.075 Uiso 0.328(8) 1 calc PR B 2
C9A C 1.1231(6) 0.4266(10) 0.2454(6) 0.062(3) Uani 0.328(8) 1 d PD B 2
H9A1 H 1.1762 0.4197 0.2988 0.074 Uiso 0.328(8) 1 calc PR B 2
H9A2 H 1.0822 0.4456 0.2670 0.074 Uiso 0.328(8) 1 calc PR B 2
C10 C 1.18391(14) 0.5960(3) 0.16089(17) 0.0614(8) Uani 1 1 d D B .
H10A H 1.1921 0.5287 0.1203 0.074 Uiso 1 1 calc R . .
H10B H 1.2356 0.6071 0.2158 0.074 Uiso 1 1 calc R . .
C11 C 1.15867(16) 0.7307(3) 0.11490(17) 0.0608(7) Uani 1 1 d . . .
H11A H 1.1491 0.7978 0.1546 0.073 Uiso 1 1 calc R B .
H11B H 1.2013 0.7688 0.1008 0.073 Uiso 1 1 calc R . .
N1 N 0.79180(13) 0.7879(2) 0.13902(13) 0.0500(5) Uani 1 1 d . . .
F1 F 0.87924(12) 0.96764(16) 0.18547(12) 0.0761(5) Uani 1 1 d . . .
C1 C 0.86025(16) 0.8400(2) 0.14836(15) 0.0482(6) Uani 1 1 d . . .
F2 F 0.98179(9) 0.83717(15) 0.13505(11) 0.0638(4) Uani 1 1 d . . .
C2 C 0.91257(13) 0.7755(2) 0.12306(15) 0.0412(5) Uani 1 1 d . . .
N2 N 0.94243(12) 0.5774(2) 0.05419(15) 0.0464(5) Uani 1 1 d . . .
H2B H 0.9888(18) 0.606(3) 0.0713(19) 0.059(8) Uiso 1 1 d . . .
H2A H 0.9341(16) 0.494(3) 0.0419(18) 0.053(7) Uiso 1 1 d . . .
C3 C 0.89507(12) 0.6434(2) 0.08352(13) 0.0352(4) Uani 1 1 d . . .
F3 F 0.79909(8) 0.46160(14) 0.03751(10) 0.0540(4) Uani 1 1 d . . .
C4 C 0.82206(12) 0.5895(2) 0.07419(14) 0.0378(4) Uani 1 1 d . . .
F4 F 0.70513(9) 0.60765(19) 0.09252(11) 0.0662(4) Uani 1 1 d . . .
C5 C 0.77498(13) 0.6640(3) 0.10250(15) 0.0446(5) Uani 1 1 d . . .
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'
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
C11 O1 C6 112.8(2) 5_765
C7 O2 C8 122.0(3) .
C7 O2 C8A 86.3(4) .
C8 O2 C8A 39.7(4) .
C9 O3 C10 104.9(3) .
C9 O3 C9A 33.5(3) .
C10 O3 C9A 133.5(4) .
O1 C6 C7 109.6(2) .
O1 C6 H6A 109.7 .
C7 C6 H6A 109.7 .
O1 C6 H6B 109.7 .
C7 C6 H6B 109.7 .
H6A C6 H6B 108.2 .
O2 C7 C6 108.6(2) .
O2 C7 C8A 49.2(3) .
C6 C7 C8A 156.0(3) .
O2 C7 H7A 110.0 .
C6 C7 H7A 110.0 .
C8A C7 H7A 89.1 .
O2 C7 H7B 110.0 .
C6 C7 H7B 110.0 .
C8A C7 H7B 75.8 .
H7A C7 H7B 108.3 .
O2 C8 C9 110.4(3) .
O2 C8 H8A 109.6 .
C9 C8 H8A 109.6 .
O2 C8 H8B 109.6 .
C9 C8 H8B 109.6 .
H8A C8 H8B 108.1 .
O3 C9 C8 106.9(4) .
O3 C9 H9A 110.3 .
C8 C9 H9A 110.3 .
O3 C9 H9B 110.3 .
C8 C9 H9B 110.3 .
H9A C9 H9B 108.6 .
C9A C8A O2 98.3(7) .
C9A C8A C7 142.0(7) .
O2 C8A C7 44.5(3) .
C9A C8A H8A1 112.1 .
O2 C8A H8A1 112.1 .
C7 C8A H8A1 93.0 .
C9A C8A H8A2 112.1 .
O2 C8A H8A2 112.1 .
C7 C8A H8A2 83.2 .
H8A1 C8A H8A2 109.8 .
C8A C9A O3 110.1(8) .
C8A C9A H9A1 109.6 .
O3 C9A H9A1 109.6 .
C8A C9A H9A2 109.6 .
O3 C9A H9A2 109.6 .
H9A1 C9A H9A2 108.2 .
O3 C10 C11 110.3(2) .
O3 C10 H10A 109.6 .
C11 C10 H10A 109.6 .
O3 C10 H10B 109.6 .
C11 C10 H10B 109.6 .
H10A C10 H10B 108.1 .
O1 C11 C10 108.5(2) 5_765
O1 C11 H11A 110.0 5_765
C10 C11 H11A 110.0 .
O1 C11 H11B 110.0 5_765
C10 C11 H11B 110.0 .
H11A C11 H11B 108.4 .
C5 N1 C1 114.96(19) .
N1 C1 F1 116.5(2) .
N1 C1 C2 125.2(2) .
F1 C1 C2 118.3(2) .
F2 C2 C1 121.3(2) .
F2 C2 C3 118.39(18) .
C1 C2 C3 120.3(2) .
C3 N2 H2B 118(2) .
C3 N2 H2A 117.9(19) .
H2B N2 H2A 117(3) .
N2 C3 C4 123.23(19) .
N2 C3 C2 123.1(2) .
C4 C3 C2 113.66(18) .
F3 C4 C5 120.49(19) .
F3 C4 C3 118.98(18) .
C5 C4 C3 120.5(2) .
N1 C5 F4 116.2(2) .
N1 C5 C4 125.3(2) .
F4 C5 C4 118.5(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.404(3) 5_765
O1 C6 1.442(3) .
O2 C7 1.386(4) .
O2 C8 1.481(4) .
O2 C8A 1.498(8) .
O3 C9 1.413(4) .
O3 C10 1.434(3) .
O3 C9A 1.502(10) .
C6 C7 1.472(5) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8A 1.974(9) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.487(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C8A C9A 1.504(13) .
C8A H8A1 0.9900 .
C8A H8A2 0.9900 .
C9A H9A1 0.9900 .
C9A H9A2 0.9900 .
C10 C11 1.467(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 O1 1.404(3) 5_765
C11 H11A 0.9900 .
C11 H11B 0.9900 .
N1 C5 1.306(3) .
N1 C1 1.311(3) .
F1 C1 1.345(3) .
C1 C2 1.366(3) .
F2 C2 1.348(3) .
C2 C3 1.397(3) .
N2 C3 1.338(3) .
N2 H2B 0.83(3) .
N2 H2A 0.83(3) .
C3 C4 1.396(3) .
F3 C4 1.351(2) .
C4 C5 1.364(3) .
F4 C5 1.348(3) .
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
C11 O1 C6 C7 170.4(2) 5_765 .
C8 O2 C7 C6 172.5(3) . .
C8A O2 C7 C6 -169.2(4) . .
C8 O2 C7 C8A -18.3(4) . .
O1 C6 C7 O2 61.1(3) . .
O1 C6 C7 C8A 40.8(11) . .
C7 O2 C8 C9 76.5(4) . .
C8A O2 C8 C9 47.2(6) . .
C10 O3 C9 C8 -174.7(3) . .
C9A O3 C9 C8 32.9(6) . .
O2 C8 C9 O3 76.2(4) . .
C7 O2 C8A C9A 171.4(7) . .
C8 O2 C8A C9A -33.2(5) . .
C8 O2 C8A C7 155.4(5) . .
O2 C7 C8A C9A -13.9(12) . .
C6 C7 C8A C9A 12(2) . .
C6 C7 C8A O2 25.8(11) . .
O2 C8A C9A O3 -83.2(9) . .
C7 C8A C9A O3 -73.3(16) . .
C9 O3 C9A C8A -45.4(7) . .
C10 O3 C9A C8A -83.5(8) . .
C9 O3 C10 C11 170.9(2) . .
C9A O3 C10 C11 -168.4(5) . .
O3 C10 C11 O1 -62.6(3) . 5_765
C5 N1 C1 F1 179.8(2) . .
C5 N1 C1 C2 0.2(3) . .
N1 C1 C2 F2 179.8(2) . .
F1 C1 C2 F2 0.3(3) . .
N1 C1 C2 C3 0.2(4) . .
F1 C1 C2 C3 -179.44(19) . .
F2 C2 C3 N2 -2.4(3) . .
C1 C2 C3 N2 177.3(2) . .
F2 C2 C3 C4 -179.90(19) . .
C1 C2 C3 C4 -0.2(3) . .
N2 C3 C4 F3 3.1(3) . .
C2 C3 C4 F3 -179.39(18) . .
N2 C3 C4 C5 -177.6(2) . .
C2 C3 C4 C5 0.0(3) . .
C1 N1 C5 F4 179.7(2) . .
C1 N1 C5 C4 -0.4(3) . .
F3 C4 C5 N1 179.7(2) . .
C3 C4 C5 N1 0.4(3) . .
F3 C4 C5 F4 -0.4(3) . .
C3 C4 C5 F4 -179.72(19) . .
