#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:08:58 +0100 (dom 17 de nov de 2019) $
#$Revision: 230389 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/73/7057348.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_7057348
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(C7 H9 N)'
_chemical_formula_sum            'C10 H9 F2 I N'
_chemical_formula_weight         308.08
_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   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                88.673(7)
_cell_angle_beta                 64.626(9)
_cell_angle_gamma                66.878(8)
_cell_formula_units_Z            2
_cell_length_a                   8.2478(7)
_cell_length_b                   8.7243(8)
_cell_length_c                   8.9978(8)
_cell_measurement_reflns_used    4404
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.9297
_cell_measurement_theta_min      4.3930
_cell_volume                     529.73(10)
_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 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0193
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3477
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         4.421
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.010
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28007
_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    1.931
_exptl_crystal_description       block
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0244
_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)+(0.0414P)²+0.3918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1676
_reflns_number_total             1799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj01368c2.cif
_cod_data_source_block           I14
_cod_depositor_comments
'Adding full bibliography for 7057346--7057365.cif.'
_cod_original_cell_volume        529.73(9)
_cod_database_code               7057348
_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 0.22876(3) 0.27365(3) 0.35933(3) 0.03333(11) Uani 1 1 d . .
F1 F -0.1305(3) 0.2427(3) 0.3349(3) 0.0400(5) Uani 1 1 d . .
F2 F 0.3086(3) -0.0397(3) 0.5551(3) 0.0401(5) Uani 1 1 d . .
C4 C 0.3229(5) 0.7556(4) 0.1094(4) 0.0291(8) Uani 1 1 d . .
C5 C 0.2749(5) 0.6285(5) 0.1802(5) 0.0335(8) Uani 1 1 d . .
H9 H 0.1703 0.6162 0.1752 0.040 Uiso 1 1 calc R U
N1 N 0.3675(5) 0.5227(4) 0.2547(4) 0.0350(7) Uani 1 1 d . .
C3 C 0.4772(5) 0.7716(4) 0.1176(4) 0.0314(8) Uani 1 1 d . .
H5 H 0.5140 0.8565 0.0718 0.038 Uiso 1 1 calc R U
C9 C -0.0630(5) 0.1228(4) 0.4178(4) 0.0291(8) Uani 1 1 d . .
C1 C 0.5169(6) 0.5411(5) 0.2602(5) 0.0338(8) Uani 1 1 d . .
H1 H 0.5835 0.4673 0.3123 0.041 Uiso 1 1 calc R U
C2 C 0.5791(5) 0.6625(5) 0.1935(5) 0.0336(8) Uani 1 1 d . .
C10 C 0.1554(5) -0.0177(5) 0.5267(4) 0.0299(8) Uani 1 1 d . .
C8 C 0.0951(5) 0.1085(4) 0.4416(4) 0.0277(7) Uani 1 1 d . .
C7 C 0.2111(6) 0.8696(5) 0.0255(5) 0.0436(10) Uani 1 1 d . .
H8 H 0.1847 0.9845 0.0574 0.065 Uiso 1 1 calc R U
H7 H 0.0882 0.8609 0.0591 0.065 Uiso 1 1 calc R U
H6 H 0.2888 0.8365 -0.0935 0.065 Uiso 1 1 calc R U
C6 C 0.7517(7) 0.6763(7) 0.2007(6) 0.0535(12) Uani 1 1 d . .
H2 H 0.8120 0.5840 0.2474 0.080 Uiso 1 1 calc R U
H4 H 0.7062 0.7816 0.2693 0.080 Uiso 1 1 calc R U
H3 H 0.8472 0.6723 0.0899 0.080 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
C3 C4 C5 117.0(3) . .
C3 C4 C7 122.0(4) . .
C5 C4 C7 121.0(4) . .
N1 C5 C4 124.4(4) . .
C5 N1 C1 117.2(3) . .
C4 C3 C2 120.4(4) . .
F1 C9 C8 119.7(3) . .
F1 C9 C10 118.0(3) . 2_556
C8 C9 C10 122.3(3) . 2_556
N1 C1 C2 123.8(3) . .
C1 C2 C3 117.2(3) . .
C1 C2 C6 121.8(4) . .
C3 C2 C6 121.1(4) . .
F2 C10 C9 118.7(3) . 2_556
F2 C10 C8 119.6(3) . .
C9 C10 C8 121.6(3) 2_556 .
C9 C8 C10 116.0(3) . .
C9 C8 I1 121.3(3) . .
C10 C8 I1 122.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C8 2.083(4) .
F1 C9 1.350(4) .
F2 C10 1.335(4) .
C4 C3 1.366(5) .
C4 C5 1.374(6) .
C4 C7 1.500(5) .
C5 N1 1.320(5) .
N1 C1 1.324(5) .
C3 C2 1.383(5) .
C9 C8 1.368(5) .
C9 C10 1.368(6) 2_556
C1 C2 1.371(6) .
C2 C6 1.504(6) .
C10 C9 1.368(6) 2_556
C10 C8 1.380(5) .
