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#$Date: 2019-11-07 21:38:55 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/34/7233432.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_7233432
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(C9 H4 Cl F3 N2), C12 H24 O6'
_chemical_formula_sum            'C30 H32 Cl2 F6 N4 O6'
_chemical_formula_weight         729.49
_chemical_melting_point          415
_chemical_name_systematic
;
7-amino-2-chloro-5,6,8-trifluoroquinoline 18-crown-6, associate 2:1
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.472(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.5421(5)
_cell_length_b                   9.4386(3)
_cell_length_c                   14.5435(6)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.94
_cell_measurement_theta_min      2.53
_cell_volume                     1651.00(11)
_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 0.999
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36550
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.140
_diffrn_reflns_theta_min         2.530
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.8374
_exptl_absorpt_correction_T_min  0.7995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4872
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0519
_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)+(0.0899P)²+0.8013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1726
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3681
_reflns_number_total             4872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00645a2.cif
_cod_data_source_block           2Gxcr-M15_1
_cod_depositor_comments
'Adding full bibliography for 7233421--7233432.cif.'
_cod_database_code               7233432
_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   0.878
_shelx_estimated_absorpt_t_max   0.909
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.73146(4) 0.42712(7) 0.23444(4) 0.06643(19) Uani 1 1 d . .
F1 F 0.40810(13) 0.89452(15) -0.06333(12) 0.0816(4) Uani 1 1 d . .
O1 O -0.07919(14) 0.54506(19) -0.19613(11) 0.0676(4) Uani 1 1 d . .
N1 N 0.52862(11) 0.50322(15) 0.15258(10) 0.0425(3) Uani 1 1 d . .
C1 C 0.63132(13) 0.53576(19) 0.15937(11) 0.0433(3) Uani 1 1 d . .
F2 F 0.19522(11) 0.82780(15) -0.07678(11) 0.0715(4) Uani 1 1 d . .
O2 O -0.06730(13) 0.77974(19) -0.07137(13) 0.0712(4) Uani 1 1 d . .
N2 N 0.14080(14) 0.6037(2) 0.02127(17) 0.0691(5) Uani 1 1 d D .
H2A H 0.0937(19) 0.656(3) -0.0156(16) 0.077(8) Uiso 1 1 d D .
H2B H 0.130(2) 0.539(2) 0.0578(17) 0.083(9) Uiso 1 1 d D .
C2 C 0.66788(15) 0.6475(2) 0.11247(14) 0.0508(4) Uani 1 1 d . .
H2 H 0.7431 0.6634 0.1203 0.061 Uiso 1 1 calc R U
F3 F 0.31207(10) 0.44424(14) 0.13253(11) 0.0711(4) Uani 1 1 d . .
O3 O -0.04613(13) 0.70872(17) 0.12425(12) 0.0656(4) Uani 1 1 d . .
C3 C 0.58839(16) 0.7318(2) 0.05495(15) 0.0520(4) Uani 1 1 d . .
H3 H 0.6089 0.8079 0.0231 0.062 Uiso 1 1 calc R U
C3A C 0.47494(13) 0.70376(17) 0.04372(11) 0.0405(3) Uani 1 1 d . .
C4 C 0.38609(16) 0.78301(18) -0.01364(14) 0.0489(4) Uani 1 1 d . .
C5 C 0.27847(15) 0.74981(19) -0.02073(13) 0.0480(4) Uani 1 1 d . .
C6 C 0.24850(13) 0.63405(19) 0.02856(12) 0.0445(3) Uani 1 1 d . .
C7A C 0.44821(12) 0.58639(15) 0.09401(10) 0.0361(3) Uani 1 1 d . .
C7 C 0.33648(13) 0.55634(17) 0.08452(12) 0.0428(3) Uani 1 1 d . .
C8 C -0.0748(2) 0.6862(3) -0.22477(18) 0.0818(8) Uani 1 1 d . .
H8A H -0.1124 0.6952 -0.2927 0.098 Uiso 1 1 calc R U
H8B H 0.0021 0.7145 -0.2143 0.098 Uiso 1 1 calc R U
C9 C -0.1284(2) 0.7795(3) -0.1697(2) 0.0781(7) Uani 1 1 d . .
H9A H -0.1325 0.8752 -0.1948 0.094 Uiso 1 1 calc R U
H9B H -0.2035 0.7469 -0.1765 0.094 Uiso 1 1 calc R U
C10 C -0.1218(2) 0.8496(3) -0.0134(2) 0.0798(8) Uani 1 1 d . .
H10A H -0.1920 0.8030 -0.0178 0.096 Uiso 1 1 calc R U
H10B H -0.1373 0.9466 -0.0350 0.096 Uiso 1 1 calc R U
C11 C -0.0511(3) 0.8481(3) 0.0875(2) 0.0814(8) Uani 1 1 d . .
H11A H 0.0231 0.8807 0.0905 0.098 Uiso 1 1 calc R U
H11B H -0.0820 0.9115 0.1258 0.098 Uiso 1 1 calc R U
C12 C 0.0324(2) 0.6966(3) 0.2153(2) 0.0816(8) Uani 1 1 d . .
H12A H 0.0133 0.7613 0.2600 0.098 Uiso 1 1 calc R U
H12B H 0.1057 0.7216 0.2108 0.098 Uiso 1 1 calc R U
C13 C 0.0333(2) 0.5488(4) 0.25065(17) 0.0812(8) Uani 1 1 d . .
H13A H 0.0766 0.5444 0.3174 0.097 Uiso 1 1 calc R U
H13B H -0.0421 0.5197 0.2465 0.097 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
C8 O1 C13 111.8(2) . 3_565
C1 N1 C7A 116.82(14) . .
N1 C1 C2 126.46(16) . .
N1 C1 Cl1 115.50(13) . .
C2 C1 Cl1 118.04(13) . .
C10 O2 C9 113.2(2) . .
C6 N2 H2A 116(2) . .
C6 N2 H2B 116(2) . .
H2A N2 H2B 128(3) . .
C3 C2 C1 117.07(16) . .
C3 C2 H2 121.5 . .
C1 C2 H2 121.5 . .
C12 O3 C11 111.9(2) . .
C2 C3 C3A 120.02(16) . .
C2 C3 H3 120.0 . .
C3A C3 H3 120.0 . .
C4 C3A C3 125.00(16) . .
C4 C3A C7A 117.30(15) . .
C3 C3A C7A 117.70(15) . .
F1 C4 C5 119.24(17) . .
F1 C4 C3A 119.06(17) . .
C5 C4 C3A 121.71(15) . .
F2 C5 C4 120.13(16) . .
F2 C5 C6 117.20(16) . .
C4 C5 C6 122.67(16) . .
N2 C6 C7 123.07(17) . .
N2 C6 C5 121.72(17) . .
C7 C6 C5 115.21(15) . .
N1 C7A C7 119.11(14) . .
N1 C7A C3A 121.92(14) . .
C7 C7A C3A 118.97(14) . .
F3 C7 C6 117.42(14) . .
F3 C7 C7A 118.43(14) . .
C6 C7 C7A 124.15(15) . .
O1 C8 C9 110.1(2) . .
O1 C8 H8A 109.6 . .
C9 C8 H8A 109.6 . .
O1 C8 H8B 109.6 . .
C9 C8 H8B 109.6 . .
H8A C8 H8B 108.2 . .
O2 C9 C8 110.5(2) . .
O2 C9 H9A 109.6 . .
C8 C9 H9A 109.6 . .
O2 C9 H9B 109.6 . .
C8 C9 H9B 109.6 . .
H9A C9 H9B 108.1 . .
O2 C10 C11 109.7(2) . .
O2 C10 H10A 109.7 . .
C11 C10 H10A 109.7 . .
O2 C10 H10B 109.7 . .
C11 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
O3 C11 C10 109.4(2) . .
O3 C11 H11A 109.8 . .
C10 C11 H11A 109.8 . .
O3 C11 H11B 109.8 . .
C10 C11 H11B 109.8 . .
H11A C11 H11B 108.2 . .
O3 C12 C13 109.5(2) . .
O3 C12 H12A 109.8 . .
C13 C12 H12A 109.8 . .
O3 C12 H12B 109.8 . .
C13 C12 H12B 109.8 . .
H12A C12 H12B 108.2 . .
O1 C13 C12 111.0(2) 3_565 .
O1 C13 H13A 109.4 3_565 .
C12 C13 H13A 109.4 . .
O1 C13 H13B 109.4 3_565 .
C12 C13 H13B 109.4 . .
H13A C13 H13B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.7445(18) .
F1 C4 1.349(2) .
O1 C8 1.402(3) .
O1 C13 1.416(3) 3_565
N1 C1 1.300(2) .
N1 C7A 1.368(2) .
C1 C2 1.402(3) .
F2 C5 1.347(2) .
O2 C10 1.393(3) .
O2 C9 1.418(3) .
N2 C6 1.355(2) .
N2 H2A 0.837(10) .
N2 H2B 0.842(10) .
C2 C3 1.362(3) .
C2 H2 0.9300 .
F3 C7 1.3498(19) .
O3 C12 1.414(3) .
O3 C11 1.415(3) .
C3 C3A 1.411(2) .
C3 H3 0.9300 .
C3A C4 1.404(2) .
C3A C7A 1.419(2) .
C4 C5 1.361(3) .
C5 C6 1.415(3) .
C6 C7 1.382(2) .
C7A C7 1.398(2) .
C8 C9 1.475(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.483(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.486(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 O1 1.416(3) 3_565
C13 H13A 0.9700 .
C13 H13B 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
C7A N1 C1 C2 -0.1(3) . .
C7A N1 C1 Cl1 -179.85(11) . .
N1 C1 C2 C3 0.9(3) . .
Cl1 C1 C2 C3 -179.38(14) . .
C1 C2 C3 C3A -0.8(3) . .
C2 C3 C3A C4 -179.87(18) . .
C2 C3 C3A C7A 0.0(3) . .
C3 C3A C4 F1 0.6(3) . .
C7A C3A C4 F1 -179.34(16) . .
C3 C3A C4 C5 -179.76(18) . .
C7A C3A C4 C5 0.3(3) . .
F1 C4 C5 F2 0.0(3) . .
C3A C4 C5 F2 -179.71(17) . .
F1 C4 C5 C6 179.58(18) . .
C3A C4 C5 C6 -0.1(3) . .
F2 C5 C6 N2 -1.1(3) . .
C4 C5 C6 N2 179.3(2) . .
F2 C5 C6 C7 179.46(16) . .
C4 C5 C6 C7 -0.2(3) . .
C1 N1 C7A C7 -179.72(15) . .
C1 N1 C7A C3A -0.7(2) . .
C4 C3A C7A N1 -179.32(15) . .
C3 C3A C7A N1 0.8(2) . .
C4 C3A C7A C7 -0.3(2) . .
C3 C3A C7A C7 179.77(16) . .
N2 C6 C7 F3 0.9(3) . .
C5 C6 C7 F3 -179.61(16) . .
N2 C6 C7 C7A -179.30(19) . .
C5 C6 C7 C7A 0.2(3) . .
N1 C7A C7 F3 -1.1(2) . .
C3A C7A C7 F3 179.85(15) . .
N1 C7A C7 C6 179.09(16) . .
C3A C7A C7 C6 0.1(3) . .
C13 O1 C8 C9 177.2(2) 3_565 .
C10 O2 C9 C8 -171.4(2) . .
O1 C8 C9 O2 65.6(3) . .
C9 O2 C10 C11 -178.5(2) . .
C12 O3 C11 C10 171.6(2) . .
O2 C10 C11 O3 -70.3(3) . .
C11 O3 C12 C13 179.5(2) . .
O3 C12 C13 O1 69.5(3) . 3_565
