#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:38:55 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/34/7233429.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_7233429
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 Cl F3 N2), C12 H24 O6'
_chemical_formula_sum            'C22 H28 Cl2 F6 N4 O6'
_chemical_formula_weight         629.38
_chemical_melting_point          393
_chemical_name_systematic
;
2-amino-4-chloro-3,5,6-trifluoropyridine 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                 109.214(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.3524(11)
_cell_length_b                   8.0294(3)
_cell_length_c                   16.3762(8)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.63
_cell_volume                     2775.4(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 0.997
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35519
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.762
_diffrn_reflns_theta_min         1.930
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.8373
_exptl_absorpt_correction_T_min  0.7874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0435
_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)+(0.0851P)²+2.6871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2658
_reflns_number_total             3584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00645a2.cif
_cod_data_source_block           2Excr-M18_2
_cod_depositor_comments
'Adding full bibliography for 7233421--7233432.cif.'
_cod_database_code               7233429
_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   0.844
_shelx_estimated_absorpt_t_max   0.954
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
O1 O 0.25886(6) 0.53682(18) 0.41118(9) 0.0435(3) Uani 1 1 d . .
O2 O 0.34719(7) 0.48537(17) 0.58189(9) 0.0436(3) Uani 1 1 d . .
O3 O 0.31222(7) 0.23142(18) 0.68299(9) 0.0473(3) Uani 1 1 d . .
C6 C 0.31737(9) 0.6241(2) 0.44533(14) 0.0449(5) Uani 1 1 d . .
H6A H 0.3139 0.7330 0.4185 0.054 Uiso 1 1 calc R U
H6B H 0.3508 0.5630 0.4328 0.054 Uiso 1 1 calc R U
C7 C 0.33326(10) 0.6432(2) 0.54083(14) 0.0449(5) Uani 1 1 d . .
H7A H 0.3696 0.7163 0.5630 0.054 Uiso 1 1 calc R U
H7B H 0.2978 0.6933 0.5534 0.054 Uiso 1 1 calc R U
C8 C 0.35526(11) 0.4981(3) 0.67098(14) 0.0504(5) Uani 1 1 d . .
H8A H 0.3173 0.5447 0.6784 0.060 Uiso 1 1 calc R U
H8B H 0.3904 0.5720 0.6988 0.060 Uiso 1 1 calc R U
C9 C 0.36796(11) 0.3303(3) 0.71210(13) 0.0514(5) Uani 1 1 d . .
H9A H 0.4018 0.2764 0.6972 0.062 Uiso 1 1 calc R U
H9B H 0.3813 0.3416 0.7745 0.062 Uiso 1 1 calc R U
C10 C 0.32325(11) 0.0645(3) 0.71176(13) 0.0494(5) Uani 1 1 d . .
H10A H 0.3399 0.0616 0.7744 0.059 Uiso 1 1 calc R U
H10B H 0.3542 0.0139 0.6896 0.059 Uiso 1 1 calc R U
C11 C 0.26262(11) -0.0301(3) 0.68065(14) 0.0483(5) Uani 1 1 d . .
H11A H 0.2690 -0.1421 0.7041 0.058 Uiso 1 1 calc R U
H11B H 0.2310 0.0240 0.7003 0.058 Uiso 1 1 calc R U
Cl1 Cl 0.01184(3) 0.13412(9) 0.60760(5) 0.0732(2) Uani 1 1 d . .
N1 N 0.09858(8) 0.4237(2) 0.44180(11) 0.0467(4) Uani 1 1 d . .
C1 C 0.13614(9) 0.3656(2) 0.51796(13) 0.0394(4) Uani 1 1 d . .
F1 F 0.14628(6) 0.22798(19) 0.64936(8) 0.0567(4) Uani 1 1 d . .
N2 N 0.19918(9) 0.3960(3) 0.54289(15) 0.0522(5) Uani 1 1 d . .
H2B H 0.2113(13) 0.427(4) 0.5029(18) 0.061(8) Uiso 1 1 d . .
H2A H 0.2254(14) 0.336(4) 0.587(2) 0.066(8) Uiso 1 1 d . .
C2 C 0.10889(9) 0.2802(2) 0.57143(12) 0.0395(4) Uani 1 1 d . .
F2 F -0.05521(6) 0.2823(2) 0.43585(11) 0.0729(5) Uani 1 1 d . .
C3 C 0.04482(9) 0.2475(3) 0.54457(14) 0.0433(4) Uani 1 1 d . .
F3 F 0.00236(8) 0.4552(3) 0.34115(10) 0.0797(5) Uani 1 1 d . .
C4 C 0.00807(9) 0.3065(3) 0.46523(14) 0.0477(5) Uani 1 1 d . .
C5 C 0.03787(10) 0.3939(3) 0.41798(14) 0.0491(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'
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
C11 O1 C6 112.37(15) 7_556
C8 O2 C7 110.96(16) .
C10 O3 C9 112.33(16) .
O1 C6 C7 109.43(16) .
O2 C7 C6 110.10(16) .
O2 C8 C9 109.96(17) .
O3 C9 C8 109.73(18) .
O3 C10 C11 109.26(17) .
O1 C11 C10 109.50(16) 7_556
C5 N1 C1 119.11(18) .
N1 C1 N2 119.32(19) .
N1 C1 C2 119.05(17) .
N2 C1 C2 121.58(19) .
F1 C2 C3 120.02(18) .
F1 C2 C1 119.02(17) .
C3 C2 C1 120.95(18) .
C4 C3 C2 118.13(18) .
C4 C3 Cl1 120.74(16) .
C2 C3 Cl1 121.12(16) .
F2 C4 C5 121.3(2) .
F2 C4 C3 121.2(2) .
C5 C4 C3 117.45(18) .
N1 C5 F3 116.7(2) .
N1 C5 C4 125.2(2) .
F3 C5 C4 118.08(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.421(2) 7_556
O1 C6 1.426(2) .
O2 C8 1.414(3) .
O2 C7 1.421(2) .
O3 C10 1.415(3) .
O3 C9 1.421(3) .
C6 C7 1.493(3) .
C8 C9 1.491(3) .
C10 C11 1.489(3) .
C11 O1 1.421(2) 7_556
Cl1 C3 1.714(2) .
N1 C5 1.305(3) .
N1 C1 1.338(3) .
C1 N2 1.354(3) .
C1 C2 1.399(3) .
F1 C2 1.342(2) .
C2 C3 1.378(3) .
F2 C4 1.350(2) .
C3 C4 1.373(3) .
F3 C5 1.341(3) .
C4 C5 1.369(3) .
