#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:08:58 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230389 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/73/7057360.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_7057360
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         'C13 H9 N, C6 F4 I2'
_chemical_formula_sum            'C19 H9 F4 I2 N'
_chemical_formula_weight         581.07
_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   geom
_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                90.000(5)
_cell_angle_beta                 107.704(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   11.102(5)
_cell_length_b                   9.839(5)
_cell_length_c                   17.118(5)
_cell_measurement_reflns_used    4259
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      31.3604
_cell_measurement_theta_min      3.9002
_cell_volume                     1781.3(13)
_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_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0236
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8256
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.903
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29909
_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    2.167
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0256
_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)+(0.0270P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0530
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2348
_reflns_number_total             3108
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj01368c2.cif
_cod_data_source_block           V13
_cod_depositor_comments
'Adding full bibliography for 7057346--7057365.cif.'
_cod_database_code               7057360
_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+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
I1 I 0.64043(2) 0.60398(2) 0.46933(2) 0.04612(9) Uani 1 1 d . .
I2 I 0.63916(3) 0.22570(3) 0.19001(2) 0.06093(11) Uani 1 1 d . .
F4 F 0.9018(2) 0.4457(2) 0.53742(13) 0.0606(6) Uani 1 1 d . .
F3 F 1.0158(2) 0.2574(3) 0.47258(16) 0.0769(8) Uani 1 1 d . .
F1 F 0.55470(19) 0.4444(2) 0.29807(13) 0.0552(6) Uani 1 1 d . .
F2 F 0.9043(2) 0.1612(3) 0.32118(16) 0.0814(8) Uani 1 1 d . .
N1 N 0.4732(3) 0.1869(3) 0.44734(18) 0.0415(7) Uani 1 1 d . .
C25 C 0.9012(4) 0.3042(4) 0.4284(3) 0.0507(11) Uani 1 1 d . .
C8 C 0.4594(4) 0.0430(4) 0.3291(2) 0.0453(10) Uani 1 1 d . .
C5 C 0.7774(4) 0.0055(4) 0.4834(3) 0.0549(11) Uani 1 1 d . .
H4 H 0.8172 -0.0567 0.4585 0.066 Uiso 1 1 calc R U
C24 C 0.8443(4) 0.2561(4) 0.3521(3) 0.0522(11) Uani 1 1 d . .
C26 C 0.8429(4) 0.4002(4) 0.4617(2) 0.0424(9) Uani 1 1 d . .
C1 C 0.5920(4) 0.1438(4) 0.4811(2) 0.0391(9) Uani 1 1 d . .
C7 C 0.5821(4) -0.0007(4) 0.3660(2) 0.0509(10) Uani 1 1 d . .
H5 H 0.6182 -0.0635 0.3392 0.061 Uiso 1 1 calc R U
C23 C 0.7265(3) 0.3023(4) 0.3069(2) 0.0420(9) Uani 1 1 d . .
C2 C 0.6626(4) 0.1925(4) 0.5599(2) 0.0477(10) Uani 1 1 d . .
H1 H 0.6259 0.2551 0.5865 0.057 Uiso 1 1 calc R U
C6 C 0.6518(4) 0.0478(4) 0.4421(2) 0.0436(9) Uani 1 1 d . .
C11 C 0.2102(4) 0.1307(4) 0.2637(3) 0.0587(12) Uani 1 1 d . .
H8 H 0.1265 0.1582 0.2418 0.070 Uiso 1 1 calc R U
C13 C 0.4065(4) 0.1378(3) 0.3726(2) 0.0407(9) Uani 1 1 d . .
C9 C 0.3808(5) -0.0028(4) 0.2512(2) 0.0575(11) Uani 1 1 d . .
H6 H 0.4138 -0.0637 0.2216 0.069 Uiso 1 1 calc R U
C4 C 0.8391(4) 0.0546(4) 0.5581(3) 0.0611(12) Uani 1 1 d . .
H3 H 0.9210 0.0254 0.5846 0.073 Uiso 1 1 calc R U
C3 C 0.7813(4) 0.1499(4) 0.5966(2) 0.0539(11) Uani 1 1 d . .
H2 H 0.8258 0.1837 0.6480 0.065 Uiso 1 1 calc R U
C22 C 0.6699(3) 0.3991(3) 0.3415(2) 0.0374(8) Uani 1 1 d . .
C12 C 0.2798(4) 0.1798(4) 0.3372(2) 0.0499(10) Uani 1 1 d . .
H9 H 0.2441 0.2418 0.3648 0.060 Uiso 1 1 calc R U
C10 C 0.2616(5) 0.0389(4) 0.2196(3) 0.0627(12) Uani 1 1 d . .
H7 H 0.2127 0.0074 0.1686 0.075 Uiso 1 1 calc R U
C21 C 0.7253(3) 0.4518(3) 0.4185(2) 0.0378(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
C1 N1 C13 118.5(3)
F3 C25 C24 120.5(4)
F3 C25 C26 119.2(4)
C24 C25 C26 120.3(4)
C7 C8 C9 124.5(4)
C7 C8 C13 117.9(3)
C9 C8 C13 117.6(4)
C4 C5 C6 120.4(4)
F2 C24 C25 118.8(4)
F2 C24 C23 120.4(4)
C25 C24 C23 120.8(4)
F4 C26 C25 118.9(3)
F4 C26 C21 119.8(3)
C25 C26 C21 121.3(3)
N1 C1 C2 119.3(3)
N1 C1 C6 123.0(3)
C2 C1 C6 117.7(3)
C6 C7 C8 121.0(4)
C22 C23 C24 117.8(3)
C22 C23 I2 121.8(3)
C24 C23 I2 120.4(3)
C3 C2 C1 121.2(4)
C7 C6 C5 123.4(4)
C7 C6 C1 117.5(4)
C5 C6 C1 119.1(4)
C12 C11 C10 121.4(4)
N1 C13 C12 119.1(3)
N1 C13 C8 122.1(3)
C12 C13 C8 118.8(3)
C10 C9 C8 122.1(4)
C5 C4 C3 120.8(4)
C2 C3 C4 120.7(4)
F1 C22 C23 118.4(3)
F1 C22 C21 118.5(3)
C23 C22 C21 123.1(3)
C11 C12 C13 120.5(4)
C9 C10 C11 119.7(4)
C22 C21 C26 116.6(3)
C22 C21 I1 122.8(3)
C26 C21 I1 120.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C21 2.094(4)
I2 C23 2.081(4)
F4 C26 1.338(4)
F3 C25 1.348(4)
F1 C22 1.345(4)
F2 C24 1.346(4)
N1 C1 1.338(4)
N1 C13 1.357(4)
C25 C24 1.351(5)
C25 C26 1.364(5)
C8 C7 1.385(5)
C8 C9 1.425(5)
C8 C13 1.427(5)
C5 C4 1.343(6)
C5 C6 1.420(5)
C24 C23 1.379(5)
C26 C21 1.387(5)
C1 C2 1.422(5)
C1 C6 1.430(5)
C7 C6 1.382(5)
C23 C22 1.371(5)
C2 C3 1.343(5)
C11 C12 1.351(5)
C11 C10 1.404(6)
C13 C12 1.414(5)
C9 C10 1.334(6)
C4 C3 1.408(6)
C22 C21 1.375(5)
