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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/28/4502868.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_4502868
loop_
_publ_author_name
'Pfrunder, Michael C.'
'Micallef, Aaron S.'
'Rintoul, Llewellyn'
'Arnold, Dennis P.'
'Davy, Karl J. P.'
'McMurtrie, John'
_publ_section_title
;
 Exploitation of the Menshutkin Reaction for the Controlled Assembly of
 Halogen Bonded Architectures Incorporating 1,2-Diiodotetrafluorobenzene
 and 1,3,5-Triiodotrifluorobenzene
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              714
_journal_paper_doi               10.1021/cg201017r
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         ' C6 H12 N2, 2(C6 F3 I3)'
_chemical_formula_sum            'C18 H12 F6 I6 N2'
_chemical_formula_weight         1131.70
_space_group_IT_number           15
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 107.577(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7938(5)
_cell_length_b                   9.6819(2)
_cell_length_c                   18.2902(5)
_cell_measurement_reflns_used    5190
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.6493
_cell_measurement_theta_min      3.1218
_cell_volume                     2666.25(13)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_molecular_graphics
;ORTEPIII (Farrugia, 1997)
WINGX-32 (Farrugia, 1999)
;
_computing_publication_material  'enCIFer 1.0 (CCDC, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9679
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.042
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.64717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2024
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       0.00083(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0050P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0334
_refine_ls_wR_factor_ref         0.0343
_reflns_number_gt                2486
_reflns_number_total             3096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201017r_si_002.cif
_cod_data_source_block           2
_cod_original_cell_volume        2666.26(13)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4502868
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
C1 C 0.1541(2) 0.1267(3) 0.48443(19) 0.0203(8) Uani 1 1 d .
C2 C 0.2246(2) 0.0332(3) 0.49796(18) 0.0208(8) Uani 1 1 d .
C3 C 0.2695(2) 0.0056(3) 0.44558(19) 0.0184(7) Uani 1 1 d .
C4 C 0.2420(2) 0.0748(3) 0.37668(19) 0.0204(8) Uani 1 1 d .
C5 C 0.1744(2) 0.1717(3) 0.35936(19) 0.0194(7) Uani 1 1 d .
C6 C 0.1319(2) 0.1948(3) 0.4144(2) 0.0217(8) Uani 1 1 d .
C7 C 0.0906(3) 0.1516(6) 0.7520(2) 0.0658(16) Uani 1 1 d .
H7A H 0.1471 0.2037 0.7636 0.079 Uiso 1 1 calc R
H7B H 0.1016 0.0567 0.7368 0.079 Uiso 1 1 calc R
C8 C 0.0594(3) 0.1456(5) 0.8246(2) 0.0630(16) Uani 1 1 d .
H8A H 0.0521 0.0481 0.8378 0.076 Uiso 1 1 calc R
H8B H 0.1049 0.1884 0.8683 0.076 Uiso 1 1 calc R
C9 C 0.0126(4) 0.3580(4) 0.7121(3) 0.0560(15) Uani 1 1 d .
H9A H -0.0348 0.4042 0.6712 0.067 Uiso 1 1 calc R
H9B H 0.0684 0.4103 0.7195 0.067 Uiso 1 1 calc R
N1 N 0.02404(19) 0.2180(3) 0.68892(16) 0.0220(7) Uani 1 1 d .
F1 F 0.25061(13) -0.0313(2) 0.56647(11) 0.0307(5) Uani 1 1 d .
F2 F 0.28392(13) 0.04895(18) 0.32372(11) 0.0272(5) Uani 1 1 d .
F3 F 0.06628(14) 0.2897(2) 0.39974(12) 0.0332(5) Uani 1 1 d .
I1 I 0.090231(15) 0.16844(2) 0.568086(13) 0.02204(7) Uani 1 1 d .
I2 I 0.376733(17) -0.13066(2) 0.469776(14) 0.03187(8) Uani 1 1 d .
I3 I 0.139552(18) 0.27528(3) 0.254744(15) 0.03643(8) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C6 C1 C2 115.8(3) . .
C6 C1 I1 122.4(2) . .
C2 C1 I1 121.7(2) . .
F1 C2 C3 118.6(3) . .
F1 C2 C1 117.8(3) . .
C3 C2 C1 123.5(3) . .
C4 C3 C2 117.0(3) . .
C4 C3 I2 121.0(2) . .
C2 C3 I2 122.0(2) . .
F2 C4 C3 118.5(3) . .
F2 C4 C5 118.2(3) . .
C3 C4 C5 123.2(3) . .
C4 C5 C6 116.9(3) . .
C4 C5 I3 120.5(2) . .
C6 C5 I3 122.6(3) . .
F3 C6 C5 118.5(3) . .
F3 C6 C1 118.0(3) . .
C5 C6 C1 123.5(3) . .
N1 C7 C8 110.8(3) . .
N1 C7 H7A 109.5 . .
C8 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
C8 C7 H7B 109.5 . .
H7A C7 H7B 108.1 . .
N1 C8 C7 110.1(3) 2_556 .
N1 C8 H8A 109.6 2_556 .
C7 C8 H8A 109.6 . .
N1 C8 H8B 109.6 2_556 .
C7 C8 H8B 109.6 . .
H8A C8 H8B 108.1 . .
N1 C9 C9 110.44(18) . 2_556
N1 C9 H9A 109.6 . .
C9 C9 H9A 109.6 2_556 .
N1 C9 H9B 109.6 . .
C9 C9 H9B 109.6 2_556 .
H9A C9 H9B 108.1 . .
C8 N1 C9 108.4(3) 2_556 .
C8 N1 C7 108.9(3) 2_556 .
C9 N1 C7 107.8(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.389(5) .
C1 C2 1.398(4) .
C1 I1 2.110(3) .
C2 F1 1.348(4) .
C2 C3 1.380(4) .
C3 C4 1.377(4) .
C3 I2 2.086(3) .
C4 F2 1.352(3) .
C4 C5 1.385(4) .
C5 C6 1.385(4) .
C5 I3 2.082(3) .
C6 F3 1.351(4) .
C7 N1 1.455(5) .
C7 C8 1.550(5) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 N1 1.447(5) 2_556
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 N1 1.447(4) .
C9 C9 1.555(7) 2_556
C9 H9A 0.9900 .
C9 H9B 0.9900 .
N1 C8 1.447(5) 2_556
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
C6 C1 C2 F1 177.5(3) . .
I1 C1 C2 F1 0.6(4) . .
C6 C1 C2 C3 -1.4(5) . .
I1 C1 C2 C3 -178.3(3) . .
F1 C2 C3 C4 -179.1(3) . .
C1 C2 C3 C4 -0.2(5) . .
F1 C2 C3 I2 -0.7(4) . .
C1 C2 C3 I2 178.2(2) . .
C2 C3 C4 F2 -179.2(3) . .
I2 C3 C4 F2 2.3(4) . .
C2 C3 C4 C5 2.0(5) . .
I2 C3 C4 C5 -176.5(2) . .
F2 C4 C5 C6 179.2(3) . .
C3 C4 C5 C6 -2.0(5) . .
F2 C4 C5 I3 -0.5(4) . .
C3 C4 C5 I3 178.3(3) . .
C4 C5 C6 F3 179.3(3) . .
I3 C5 C6 F3 -1.0(4) . .
C4 C5 C6 C1 0.2(5) . .
I3 C5 C6 C1 179.9(3) . .
C2 C1 C6 F3 -177.7(3) . .
I1 C1 C6 F3 -0.8(4) . .
C2 C1 C6 C5 1.4(5) . .
I1 C1 C6 C5 178.3(3) . .
N1 C7 C8 N1 -4.7(6) . 2_556
C9 C9 N1 C8 61.6(6) 2_556 2_556
C9 C9 N1 C7 -56.2(6) 2_556 .
C8 C7 N1 C8 -55.9(4) . 2_556
C8 C7 N1 C9 61.5(5) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145076
