#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:05:25 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229007 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/98/7229857.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_7229857
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(C6 H3 F4 N), C12 H24 O6'
_chemical_formula_sum            'C24 H30 F8 N2 O6'
_chemical_formula_weight         594.50
_chemical_melting_point          363
_chemical_name_systematic
; 
 2,3,5,6-tetrafluoroaniline and 18-crown-6 2:1 associate 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                117.412(2)
_cell_angle_beta                 103.573(2)
_cell_angle_gamma                100.167(2)
_cell_formula_units_Z            1
_cell_length_a                   8.5736(3)
_cell_length_b                   9.9242(4)
_cell_length_c                   10.1058(5)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.38
_cell_volume                     700.49(6)
_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      299(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19988
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9118
_exptl_absorpt_correction_T_min  0.8700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: t-BuOMe'
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.141(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3199
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0517
_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)+(0.0966P)²+0.2718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1738
_reflns_number_gt                2451
_reflns_number_total             3199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce01851g2.cif
_cod_data_source_block           2Ccr-m926
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        700.49(5)
_cod_database_code               7229857
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.0654(2) -0.21229(14) 0.58569(16) 0.0838(5) Uani 1 1 d .
F2 F 0.2232(2) -0.16656(18) 0.40531(19) 0.0971(5) Uani 1 1 d .
F3 F 0.3456(3) 0.39086(18) 0.7267(2) 0.1167(7) Uani 1 1 d .
F4 F 0.1907(2) 0.34573(14) 0.91003(16) 0.0811(4) Uani 1 1 d .
O1 O -0.26986(18) 1.13116(19) 0.99242(17) 0.0675(4) Uani 1 1 d .
O2 O -0.32987(17) 0.79850(18) 0.75003(18) 0.0679(4) Uani 1 1 d .
O3 O 0.06759(19) 1.32248(17) 1.17623(17) 0.0689(4) Uani 1 1 d .
N1 N 0.0388(3) 0.0435(2) 0.8448(2) 0.0752(6) Uani 1 1 d D
H3 H 0.044(4) 0.124(2) 0.929(2) 0.113 Uiso 1 1 d D
H1 H 0.002(4) -0.0483(19) 0.831(4) 0.113 Uiso 1 1 d D
C1 C 0.1241(2) 0.0658(2) 0.7551(2) 0.0481(4) Uani 1 1 d .
C2 C 0.1368(2) -0.0606(2) 0.6234(2) 0.0531(4) Uani 1 1 d .
C3 C 0.2177(3) -0.0367(2) 0.5306(2) 0.0617(5) Uani 1 1 d .
C4 C 0.2904(3) 0.1138(3) 0.5616(3) 0.0735(6) Uani 1 1 d .
H2 H 0.3448 0.1302 0.4981 0.088 Uiso 1 1 calc R
C5 C 0.2788(3) 0.2386(2) 0.6902(3) 0.0677(6) Uani 1 1 d .
C6 C 0.1990(2) 0.2175(2) 0.7850(2) 0.0532(4) Uani 1 1 d .
C7 C -0.0677(4) 1.3840(3) 1.1940(3) 0.0773(6) Uani 1 1 d .
H5 H -0.0304 1.4974 1.2303 0.093 Uiso 1 1 calc R
H4 H -0.1048 1.3723 1.2729 0.093 Uiso 1 1 calc R
C8 C -0.2097(3) 1.2937(3) 1.0375(3) 0.0767(6) Uani 1 1 d .
H14 H -0.3006 1.3394 1.0453 0.092 Uiso 1 1 calc R
H13 H -0.1709 1.3010 0.9576 0.092 Uiso 1 1 calc R
C9 C -0.4028(3) 1.0384(3) 0.8432(3) 0.0815(7) Uani 1 1 d .
H9A H -0.3661 1.0485 0.7634 0.098 Uiso 1 1 calc R
H9B H -0.4991 1.0766 0.8486 0.098 Uiso 1 1 calc R
C10 C -0.4533(3) 0.8688(4) 0.7975(3) 0.0852(8) Uani 1 1 d .
H11 H -0.4656 0.8619 0.8874 0.102 Uiso 1 1 calc R
H12 H -0.5623 0.8097 0.7101 0.102 Uiso 1 1 calc R
C11 C 0.3594(3) 1.3543(3) 1.2724(3) 0.0766(6) Uani 1 1 d .
H7 H 0.3652 1.3497 1.1758 0.092 Uiso 1 1 calc R
H8 H 0.4674 1.4263 1.3585 0.092 Uiso 1 1 calc R
C12 C 0.2206(3) 1.4173(3) 1.3124(3) 0.0785(7) Uani 1 1 d .
H6 H 0.2062 1.4116 1.4023 0.094 Uiso 1 1 calc R
H9 H 0.2490 1.5288 1.3416 0.094 Uiso 1 1 calc R
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
C9 O1 C8 111.77(18) .
C11 O2 C10 112.92(19) 2_577
C7 O3 C12 113.24(18) .
C1 N1 H3 120(2) .
C1 N1 H1 121(2) .
H3 N1 H1 118(3) .
N1 C1 C6 121.81(17) .
N1 C1 C2 123.02(16) .
C6 C1 C2 115.12(15) .
F1 C2 C3 118.97(17) .
F1 C2 C1 118.61(15) .
C3 C2 C1 122.41(16) .
F2 C3 C4 120.13(18) .
F2 C3 C2 118.18(18) .
C4 C3 C2 121.69(18) .
C3 C4 C5 116.46(18) .
C3 C4 H2 121.8 .
C5 C4 H2 121.8 .
F3 C5 C4 119.81(18) .
F3 C5 C6 117.35(19) .
C4 C5 C6 122.83(18) .
F4 C6 C5 120.07(16) .
F4 C6 C1 118.44(16) .
C5 C6 C1 121.49(17) .
O3 C7 C8 108.61(18) .
O3 C7 H5 110.0 .
C8 C7 H5 110.0 .
O3 C7 H4 110.0 .
C8 C7 H4 110.0 .
H5 C7 H4 108.3 .
O1 C8 C7 109.04(17) .
O1 C8 H14 109.9 .
C7 C8 H14 109.9 .
O1 C8 H13 109.9 .
C7 C8 H13 109.9 .
H14 C8 H13 108.3 .
O1 C9 C10 109.5(2) .
O1 C9 H9A 109.8 .
C10 C9 H9A 109.8 .
O1 C9 H9B 109.8 .
C10 C9 H9B 109.8 .
H9A C9 H9B 108.2 .
O2 C10 C9 110.81(19) .
O2 C10 H11 109.5 .
C9 C10 H11 109.5 .
O2 C10 H12 109.5 .
C9 C10 H12 109.5 .
H11 C10 H12 108.1 .
O2 C11 C12 110.33(18) 2_577
O2 C11 H7 109.6 2_577
C12 C11 H7 109.6 .
O2 C11 H8 109.6 2_577
C12 C11 H8 109.6 .
H7 C11 H8 108.1 .
O3 C12 C11 108.55(18) .
O3 C12 H6 110.0 .
C11 C12 H6 110.0 .
O3 C12 H9 110.0 .
C11 C12 H9 110.0 .
H6 C12 H9 108.4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.350(2) .
F2 C3 1.347(2) .
F3 C5 1.353(2) .
F4 C6 1.347(2) .
O1 C9 1.402(3) .
O1 C8 1.412(3) .
O2 C11 1.391(3) 2_577
O2 C10 1.424(3) .
O3 C7 1.413(3) .
O3 C12 1.423(3) .
N1 C1 1.358(2) .
N1 H3 0.842(10) .
N1 H1 0.843(10) .
C1 C6 1.385(2) .
C1 C2 1.391(3) .
C2 C3 1.367(3) .
C3 C4 1.367(3) .
C4 C5 1.361(3) .
C4 H2 0.9300 .
C5 C6 1.368(3) .
C7 C8 1.481(4) .
C7 H5 0.9700 .
C7 H4 0.9700 .
C8 H14 0.9700 .
C8 H13 0.9700 .
C9 C10 1.472(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H11 0.9700 .
C10 H12 0.9700 .
C11 O2 1.391(3) 2_577
C11 C12 1.492(4) .
C11 H7 0.9700 .
C11 H8 0.9700 .
C12 H6 0.9700 .
C12 H9 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
N1 C1 C2 F1 -2.1(3) .
C6 C1 C2 F1 -179.36(16) .
N1 C1 C2 C3 177.5(2) .
C6 C1 C2 C3 0.2(3) .
F1 C2 C3 F2 -0.3(3) .
C1 C2 C3 F2 -179.85(18) .
F1 C2 C3 C4 179.13(19) .
C1 C2 C3 C4 -0.4(3) .
F2 C3 C4 C5 179.8(2) .
C2 C3 C4 C5 0.4(3) .
C3 C4 C5 F3 -179.0(2) .
C3 C4 C5 C6 -0.2(4) .
F3 C5 C6 F4 -0.7(3) .
C4 C5 C6 F4 -179.6(2) .
F3 C5 C6 C1 178.82(19) .
C4 C5 C6 C1 0.0(4) .
N1 C1 C6 F4 2.2(3) .
C2 C1 C6 F4 179.57(16) .
N1 C1 C6 C5 -177.3(2) .
C2 C1 C6 C5 0.0(3) .
C12 O3 C7 C8 170.36(19) .
C9 O1 C8 C7 -178.86(19) .
O3 C7 C8 O1 63.7(3) .
C8 O1 C9 C10 176.47(18) .
C11 O2 C10 C9 171.43(19) 2_577
O1 C9 C10 O2 -74.0(2) .
C7 O3 C12 C11 -172.52(19) .
O2 C11 C12 O3 -67.1(2) 2_577
