#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:08:58 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230389 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/73/7057359.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_7057359
loop_
_publ_author_name
'Bedeković, Nikola'
'Stilinović, Vladimir'
'Friščić, Tomislav'
'Cinčić, Dominik'
_publ_section_title
;
 Comparison of isomericmeta- andpara-diiodotetrafluorobenzene as halogen
 bond donors in crystal engineering
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10584
_journal_paper_doi               10.1039/C8NJ01368C
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C6 F4 I2, C4 H10 N2'
_chemical_formula_sum            'C10 H10 F4 I2 N2'
_chemical_formula_weight         488.00
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                103.403(5)
_cell_angle_beta                 96.182(4)
_cell_angle_gamma                95.921(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1088(3)
_cell_length_b                   9.4013(6)
_cell_length_c                   12.4113(7)
_cell_measurement_reflns_used    1718
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      38.4603
_cell_measurement_theta_min      4.9337
_cell_volume                     683.27(7)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4637
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.991
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29658
_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    2.372
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.712
_refine_diff_density_min         -1.177
_refine_diff_density_rms         0.206
_refine_ls_extinction_coef       0.0400(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2386
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0517P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1855
_reflns_number_total             2386
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj01368c2.cif
_cod_data_source_block           X13
_cod_depositor_comments
'Adding full bibliography for 7057346--7057365.cif.'
_cod_database_code               7057359
_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.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I 0.72289(7) 0.19946(5) 0.58245(3) 0.04562(19) Uani 1 1 d . .
I2 I 0.74244(7) -0.28510(5) 0.83289(3) 0.0469(2) Uani 1 1 d . .
F4 F 0.3311(7) -0.1235(5) 0.9163(3) 0.0644(12) Uani 1 1 d . .
F3 F 0.1424(7) 0.1004(5) 0.8647(4) 0.0669(12) Uani 1 1 d . .
F2 F 0.3076(7) 0.2422(5) 0.7218(3) 0.0622(11) Uani 1 1 d . .
C7 C 0.5930(10) -0.1083(7) 0.7927(5) 0.0407(14) Uani 1 1 d . .
C5 C 0.5824(10) 0.0838(7) 0.6911(5) 0.0407(15) Uani 1 1 d . .
C6 C 0.6721(10) -0.0337(7) 0.7172(5) 0.0383(14) Uani 1 1 d . .
C8 C 0.4148(10) -0.0597(8) 0.8407(5) 0.0449(16) Uani 1 1 d . .
C10 C 0.4027(11) 0.1267(7) 0.7421(5) 0.0440(15) Uani 1 1 d . .
C9 C 0.3172(11) 0.0573(7) 0.8174(6) 0.0457(16) Uani 1 1 d . .
F1 F 0.8494(6) -0.0774(4) 0.6688(3) 0.0526(10) Uani 1 1 d . .
N2 N -0.0625(10) 0.4693(7) 0.8848(4) 0.0484(14) Uani 1 1 d D .
N1 N 1.0612(10) -0.3510(7) 0.5568(4) 0.0475(14) Uani 1 1 d D .
C4 C 0.1693(11) 0.5036(8) 0.9311(5) 0.0490(16) Uani 1 1 d . .
H8 H 0.2511 0.5518 0.8837 0.059 Uiso 1 1 calc R U
H7 H 0.2309 0.4136 0.9349 0.059 Uiso 1 1 calc R U
C1 C 0.8315(11) -0.4066(8) 0.5068(6) 0.0496(17) Uani 1 1 d . .
H4 H 0.7606 -0.3288 0.4836 0.059 Uiso 1 1 calc R U
H3 H 0.7490 -0.4394 0.5611 0.059 Uiso 1 1 calc R U
C3 C -0.1899(11) 0.3954(8) 0.9530(6) 0.0490(17) Uani 1 1 d . .
H10 H -0.1338 0.3037 0.9571 0.059 Uiso 1 1 calc R U
H9 H -0.3446 0.3728 0.9200 0.059 Uiso 1 1 calc R U
C2 C 0.8322(11) -0.5345(8) 0.4064(5) 0.0468(17) Uani 1 1 d . .
H2 H 0.6810 -0.5729 0.3719 0.056 Uiso 1 1 calc R U
H1 H 0.9121 -0.5011 0.3514 0.056 Uiso 1 1 calc R U
H6 H -0.102(11) 0.443(8) 0.8157(13) 0.056 Uiso 1 1 d D U
H5 H 1.042(11) -0.280(5) 0.608(4) 0.056 Uiso 1 1 d D 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'
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
C8 C7 C6 116.4(6) . .
C8 C7 I2 121.7(5) . .
C6 C7 I2 121.9(5) . .
C6 C5 C10 117.0(6) . .
C6 C5 I1 121.4(5) . .
C10 C5 I1 121.6(5) . .
F1 C6 C5 118.2(5) . .
F1 C6 C7 118.3(6) . .
C5 C6 C7 123.5(6) . .
F4 C8 C7 120.2(6) . .
F4 C8 C9 117.1(6) . .
C7 C8 C9 122.7(6) . .
F2 C10 C9 117.4(6) . .
F2 C10 C5 120.4(6) . .
C9 C10 C5 122.1(6) . .
F3 C9 C10 120.8(6) . .
F3 C9 C8 120.9(6) . .
C10 C9 C8 118.3(6) . .
C4 N2 C3 111.4(5) . .
C2 N1 C1 110.5(5) 2_746 .
N2 C4 C3 108.9(6) . 2_567
N1 C1 C2 108.6(6) . .
N2 C3 C4 108.6(5) . 2_567
N1 C2 C1 108.9(5) 2_746 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C5 2.114(6) .
I2 C7 2.108(6) .
F4 C8 1.343(7) .
F3 C9 1.328(7) .
F2 C10 1.344(7) .
C7 C8 1.365(9) .
C7 C6 1.392(8) .
C5 C6 1.370(9) .
C5 C10 1.375(9) .
C6 F1 1.349(7) .
C8 C9 1.376(9) .
C10 C9 1.374(9) .
N2 C4 1.443(9) .
N2 C3 1.451(9) .
N1 C2 1.449(9) 2_746
N1 C1 1.462(9) .
C4 C3 1.514(10) 2_567
C1 C2 1.519(10) .
C3 C4 1.514(10) 2_567
C2 N1 1.449(9) 2_746
