#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:08:58 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230389 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/73/7057350.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_7057350
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, 2(C9 H7 N)'
_chemical_formula_sum            'C24 H14 F4 I2 N2'
_chemical_formula_weight         660.18
_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
_cell_angle_beta                 100.650(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7924(11)
_cell_length_b                   6.0635(9)
_cell_length_c                   21.703(2)
_cell_measurement_reflns_used    1552
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.0040
_cell_measurement_theta_min      4.4920
_cell_volume                     1137.1(2)
_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      150(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  0.0518
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5431
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         4.341
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.972
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0455
_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)+(0.0420P)²+0.5119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1568
_reflns_number_total             1985
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj01368c2.cif
_cod_data_source_block           IV14
_cod_depositor_comments
'Adding full bibliography for 7057346--7057365.cif.'
_cod_database_code               7057350
_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 -0.21608(5) 0.80414(9) 0.87731(2) 0.0497(2) Uani 1 1 d . .
F1 F -0.2787(5) 0.3489(8) 0.9419(2) 0.0604(12) Uani 1 1 d . .
F2 F -0.1132(5) 0.1123(8) 1.03343(19) 0.0596(12) Uani 1 1 d . .
N1 N -0.1005(7) 0.5135(13) 0.7275(3) 0.0576(17) Uani 1 1 d . .
C3 C 0.1505(10) 0.2855(15) 0.8675(4) 0.059(2) Uani 1 1 d . .
H2 H 0.1007 0.1526 0.8718 0.071 Uiso 1 1 calc R U
C10 C -0.0867(8) 0.6248(13) 0.9511(3) 0.0414(17) Uani 1 1 d . .
C11 C -0.1401(7) 0.4250(13) 0.9703(3) 0.0426(17) Uani 1 1 d . .
C1 C -0.0438(9) 0.3890(15) 0.7742(3) 0.054(2) Uani 1 1 d . .
H1 H -0.0959 0.2580 0.7785 0.065 Uiso 1 1 calc R U
C6 C 0.3020(9) 0.6833(18) 0.8573(4) 0.067(2) Uani 1 1 d . .
H5 H 0.3534 0.8159 0.8545 0.080 Uiso 1 1 calc R U
C2 C 0.0894(8) 0.4327(13) 0.8192(3) 0.0445(17) Uani 1 1 d . .
C9 C -0.0277(10) 0.7106(16) 0.7233(4) 0.063(2) Uani 1 1 d . .
H7 H -0.0691 0.8051 0.6907 0.075 Uiso 1 1 calc R U
C5 C 0.3583(10) 0.5394(19) 0.9025(4) 0.069(3) Uani 1 1 d . .
H4 H 0.4486 0.5721 0.9307 0.083 Uiso 1 1 calc R U
C12 C -0.0547(8) 0.3059(13) 1.0174(3) 0.0452(17) Uani 1 1 d . .
C4 C 0.2809(10) 0.3380(19) 0.9074(4) 0.072(3) Uani 1 1 d . .
H3 H 0.3214 0.2394 0.9390 0.086 Uiso 1 1 calc R U
C7 C 0.1647(8) 0.6361(13) 0.8136(3) 0.0472(18) Uani 1 1 d . .
C8 C 0.1010(9) 0.7772(14) 0.7635(4) 0.056(2) Uani 1 1 d . .
H6 H 0.1463 0.9128 0.7583 0.067 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'
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
C1 N1 C9 116.6(7) . .
C4 C3 C2 119.6(9) . .
C4 C3 H2 120.2 . .
C2 C3 H2 120.2 . .
C12 C10 C11 116.3(6) 3_567 .
C12 C10 I1 122.6(5) 3_567 .
C11 C10 I1 121.1(5) . .
F1 C11 C12 119.5(7) . .
F1 C11 C10 119.3(6) . .
C12 C11 C10 121.2(6) . .
N1 C1 C2 126.0(8) . .
N1 C1 H1 117.0 . .
C2 C1 H1 117.0 . .
C5 C6 C7 120.8(9) . .
C5 C6 H5 119.6 . .
C7 C6 H5 119.6 . .
C3 C2 C1 123.6(8) . .
C3 C2 C7 119.8(7) . .
C1 C2 C7 116.6(7) . .
C8 C9 N1 124.2(8) . .
C8 C9 H7 117.9 . .
N1 C9 H7 117.9 . .
C6 C5 C4 120.1(9) . .
C6 C5 H4 120.0 . .
C4 C5 H4 120.0 . .
F2 C12 C11 118.1(6) . .
F2 C12 C10 119.4(6) . 3_567
C11 C12 C10 122.5(7) . 3_567
C3 C4 C5 121.6(9) . .
C3 C4 H3 119.2 . .
C5 C4 H3 119.2 . .
C8 C7 C2 117.9(7) . .
C8 C7 C6 124.0(8) . .
C2 C7 C6 118.1(8) . .
C9 C8 C7 118.7(8) . .
C9 C8 H6 120.7 . .
C7 C8 H6 120.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C10 2.090(7) .
F1 C11 1.341(8) .
F2 C12 1.353(9) .
N1 C1 1.288(9) .
N1 C9 1.367(11) .
C3 C4 1.341(12) .
C3 C2 1.405(10) .
C3 H2 0.9300 .
C10 C12 1.369(9) 3_567
C10 C11 1.391(10) .
C11 C12 1.359(9) .
C1 C2 1.405(10) .
C1 H1 0.9300 .
C6 C5 1.338(13) .
C6 C7 1.420(10) .
C6 H5 0.9300 .
C2 C7 1.416(11) .
C9 C8 1.357(11) .
C9 H7 0.9300 .
C5 C4 1.412(14) .
C5 H4 0.9300 .
C12 C10 1.369(9) 3_567
C4 H3 0.9300 .
C7 C8 1.414(10) .
C8 H6 0.9300 .
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
C12 C10 C11 F1 179.2(6) 3_567 .
I1 C10 C11 F1 -1.6(9) . .
C12 C10 C11 C12 -0.6(12) 3_567 .
I1 C10 C11 C12 178.6(5) . .
C9 N1 C1 C2 -3.1(12) . .
C4 C3 C2 C1 178.0(8) . .
C4 C3 C2 C7 -0.9(11) . .
N1 C1 C2 C3 -176.7(8) . .
N1 C1 C2 C7 2.2(11) . .
C1 N1 C9 C8 2.2(13) . .
C7 C6 C5 C4 -0.2(14) . .
F1 C11 C12 F2 0.6(10) . .
C10 C11 C12 F2 -179.5(6) . .
F1 C11 C12 C10 -179.2(6) . 3_567
C10 C11 C12 C10 0.7(12) . 3_567
C2 C3 C4 C5 0.6(13) . .
C6 C5 C4 C3 -0.1(14) . .
C3 C2 C7 C8 178.8(7) . .
C1 C2 C7 C8 -0.2(10) . .
C3 C2 C7 C6 0.6(11) . .
C1 C2 C7 C6 -178.4(7) . .
C5 C6 C7 C8 -178.1(8) . .
C5 C6 C7 C2 0.0(12) . .
N1 C9 C8 C7 -0.4(13) . .
C2 C7 C8 C9 -0.5(11) . .
C6 C7 C8 C9 177.5(8) . .
