#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:08:58 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230389 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/73/7057356.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_7057356
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         '2(C3 F2 I), C4 H9 N O'
_chemical_formula_sum            'C10 H9 F4 I2 N O'
_chemical_formula_weight         488.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                90
_cell_angle_beta                 96.422(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3023(7)
_cell_length_b                   7.2775(5)
_cell_length_c                   20.5704(18)
_cell_measurement_reflns_used    1140
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.7870
_cell_measurement_theta_min      4.6200
_cell_volume                     1383.83(19)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.1111
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5680
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         4.203
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26784
_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    2.347
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.189
_refine_ls_extinction_coef       0.0024(6)
_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   0.777
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.776
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0498
_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)+(0.0912P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1501
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1665
_reflns_number_total             2614
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj01368c2.cif
_cod_data_source_block           IX13
_cod_depositor_comments
'Adding full bibliography for 7057346--7057365.cif.'
_cod_database_code               7057356
_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+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_refinement_flags_occupancy
O1 O 0.6669(15) -0.2500 0.7795(6) 0.098(4) Uani 1 2 d S T P
N1 N 0.3867(17) -0.2500 0.8198(6) 0.065(4) Uani 1 2 d DS T P
C20 C 0.4745(15) -0.0853(15) 0.8228(5) 0.072(3) Uani 1 1 d D . .
H4 H 0.4124 0.0218 0.8169 0.086 Uiso 1 1 calc R U .
H3 H 0.5304 -0.0767 0.8654 0.086 Uiso 1 1 calc R U .
C21 C 0.5717(16) -0.0890(18) 0.7720(6) 0.087(4) Uani 1 1 d . . .
H1 H 0.6298 0.0220 0.7745 0.105 Uiso 1 1 calc R U .
H2 H 0.5155 -0.0923 0.7294 0.105 Uiso 1 1 calc R U .
I4 I 0.26795(11) 0.2500 0.40549(5) 0.0534(4) Uani 1 2 d S T P
I1 I 0.79044(11) 0.2500 1.08185(5) 0.0526(3) Uani 1 2 d S T P
I3 I 0.88943(12) 0.2500 0.52867(5) 0.0648(4) Uani 1 2 d S T P
I2 I 1.38211(12) 0.2500 0.98392(5) 0.0604(4) Uani 1 2 d S T P
F8 F 0.7164(10) 0.2500 0.6542(4) 0.064(2) Uani 1 2 d S T P
C5 C 0.945(2) 0.2500 0.8891(7) 0.056(4) Uani 1 2 d S T P
F7 F 0.4327(12) 0.2500 0.6672(4) 0.084(3) Uani 1 2 d S T P
F6 F 0.2392(10) 0.2500 0.5611(5) 0.074(3) Uani 1 2 d S T P
F2 F 1.1710(11) 0.2500 0.8511(4) 0.069(2) Uani 1 2 d S T P
F4 F 0.7181(10) 0.2500 0.9252(4) 0.075(3) Uani 1 2 d S T P
F1 F 1.1316(10) 0.2500 1.0764(4) 0.067(2) Uani 1 2 d S T P
F5 F 0.6117(10) 0.2500 0.4255(4) 0.070(2) Uani 1 2 d S T P
F3 F 0.8841(12) 0.2500 0.8269(4) 0.086(3) Uani 1 2 d S T P
C3 C 1.1589(15) 0.2500 0.9651(6) 0.038(3) Uani 1 2 d S T P
C9 C 0.4205(16) 0.2500 0.4891(7) 0.050(4) Uani 1 2 d S T P
C30 C 0.0099(16) -0.0850(17) 0.7188(6) 0.084(4) Uani 1 1 d D . .
H8 H -0.0482 0.0243 0.7089 0.101 Uiso 1 1 calc R U .
H9 H 0.0510 -0.0790 0.7642 0.101 Uiso 1 1 calc R U .
C11 C 0.4754(17) 0.2500 0.6064(7) 0.049(4) Uani 1 2 d S T P
C1 C 0.9232(16) 0.2500 1.0058(6) 0.040(3) Uani 1 2 d S T P
C10 C 0.3808(16) 0.2500 0.5503(8) 0.052(4) Uani 1 2 d S T P
C2 C 1.0689(15) 0.2500 1.0140(6) 0.041(3) Uani 1 2 d S T P
C4 C 1.0923(18) 0.2500 0.9019(7) 0.049(4) Uani 1 2 d S T P
C8 C 0.5660(16) 0.2500 0.4845(7) 0.048(3) Uani 1 2 d S T P
C6 C 0.8632(17) 0.2500 0.9394(8) 0.055(4) Uani 1 2 d S T P
N2 N -0.0807(16) -0.2500 0.7079(6) 0.072(4) Uani 1 2 d DS T P
C31 C 0.1248(19) -0.093(2) 0.6766(7) 0.106(5) Uani 1 1 d . . .
H6 H 0.1844 0.0158 0.6833 0.127 Uiso 1 1 calc R U .
H7 H 0.0824 -0.0942 0.6313 0.127 Uiso 1 1 calc R U .
C12 C 0.6233(18) 0.2500 0.6005(8) 0.056(4) Uani 1 2 d S T P
C7 C 0.6698(17) 0.2500 0.5383(8) 0.051(4) Uani 1 2 d S T P
O2 O 0.2128(16) -0.2500 0.6884(6) 0.105(5) Uani 1 2 d S T P
H5 H 0.332(4) -0.2500 0.7816(17) 0.126 Uiso 1 2 d DS U P
H10 H -0.148(4) -0.2500 0.735(3) 0.126 Uiso 1 2 d DS U P
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'
O O 0.0106 0.0060 '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
C21 O1 C21 106.1(14) . 4
C20 N1 C20 111.7(15) . 4
C20 N1 H5 107.7(16) . .
C20 N1 H5 107.7(16) 4 .
C21 C20 N1 110.4(10) . .
C21 C20 H4 109.6 . .
N1 C20 H4 109.6 . .
C21 C20 H3 109.6 . .
N1 C20 H3 109.6 . .
H4 C20 H3 108.1 . .
C20 C21 O1 110.8(11) . .
C20 C21 H1 109.5 . .
O1 C21 H1 109.5 . .
C20 C21 H2 109.5 . .
O1 C21 H2 109.5 . .
H1 C21 H2 108.1 . .
C4 C5 F3 119.3(17) . .
C4 C5 C6 119.4(14) . .
F3 C5 C6 121.3(16) . .
C2 C3 C4 116.3(13) . .
C2 C3 I2 122.8(9) . .
C4 C3 I2 120.9(11) . .
C8 C9 C10 116.1(14) . .
C8 C9 I4 121.7(12) . .
C10 C9 I4 122.2(12) . .
C31 C30 N2 108.8(11) . .
C31 C30 H8 109.9 . .
N2 C30 H8 109.9 . .
C31 C30 H9 109.9 . .
N2 C30 H9 109.9 . .
H8 C30 H9 108.3 . .
C12 C11 F7 118.4(14) . .
C12 C11 C10 118.2(14) . .
F7 C11 C10 123.4(14) . .
C2 C1 C6 113.8(14) . .
C2 C1 I1 125.0(10) . .
C6 C1 I1 121.2(11) . .
C9 C10 C11 124.7(15) . .
C9 C10 F6 121.5(14) . .
C11 C10 F6 113.9(14) . .
C1 C2 F1 116.2(13) . .
C1 C2 C3 126.3(12) . .
F1 C2 C3 117.5(12) . .
C5 C4 F2 118.2(13) . .
C5 C4 C3 121.2(14) . .
F2 C4 C3 120.6(14) . .
C9 C8 F5 118.9(12) . .
C9 C8 C7 123.5(15) . .
F5 C8 C7 117.6(13) . .
C5 C6 F4 117.9(14) . .
C5 C6 C1 123.0(15) . .
F4 C6 C1 119.1(16) . .
C30 N2 C30 109.6(14) 4 .
C30 N2 H10 109.6(17) 4 .
C30 N2 H10 109.6(17) . .
C30 C31 O2 112.6(13) . .
C30 C31 H6 109.1 . .
O2 C31 H6 109.1 . .
C30 C31 H7 109.1 . .
O2 C31 H7 109.1 . .
H6 C31 H7 107.8 . .
F8 C12 C11 119.0(15) . .
F8 C12 C7 121.6(15) . .
C11 C12 C7 119.4(14) . .
C8 C7 C12 118.2(14) . .
C8 C7 I3 122.0(12) . .
C12 C7 I3 119.8(11) . .
C31 O2 C31 108.0(16) 4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C21 1.467(15) .
O1 C21 1.467(15) 4
N1 C20 1.448(14) .
N1 C20 1.448(14) 4
N1 H5 0.890(10) .
C20 C21 1.456(17) .
C20 H4 0.9700 .
C20 H3 0.9700 .
C21 H1 0.9700 .
C21 H2 0.9700 .
I4 C9 2.103(14) .
I1 C1 2.099(14) .
I3 C7 2.074(16) .
I2 C3 2.069(14) .
F8 C12 1.326(15) .
C5 C4 1.37(2) .
C5 F3 1.339(16) .
C5 C6 1.35(2) .
F7 C11 1.354(16) .
F6 C10 1.361(18) .
F2 C4 1.342(16) .
F4 C6 1.349(17) .
F1 C2 1.350(14) .
F5 C8 1.330(17) .
C3 C2 1.379(19) .
C3 C4 1.376(18) .
C9 C8 1.37(2) .
C9 C10 1.35(2) .
C30 C31 1.451(19) .
C30 N2 1.470(15) .
C30 H8 0.9700 .
C30 H9 0.9700 .
C11 C12 1.40(2) .
C11 C10 1.371(19) .
C1 C2 1.348(19) .
C1 C6 1.42(2) .
C8 C7 1.386(19) .
N2 C30 1.470(15) 4
N2 H10 0.887(10) .
C31 O2 1.408(17) .
C31 H6 0.9700 .
C31 H7 0.9700 .
C12 C7 1.40(2) .
O2 C31 1.408(17) 4
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
C20 N1 C20 C21 54.4(15) 4 .
N1 C20 C21 O1 -59.2(14) . .
C21 O1 C21 C20 61.8(16) 4 .
C8 C9 C10 C11 0.000(6) . .
I4 C9 C10 C11 180.000(5) . .
C8 C9 C10 F6 180.000(4) . .
I4 C9 C10 F6 0.000(5) . .
C12 C11 C10 C9 0.000(7) . .
F7 C11 C10 C9 180.000(6) . .
C12 C11 C10 F6 180.000(5) . .
F7 C11 C10 F6 0.000(6) . .
C6 C1 C2 F1 180.000(7) . .
I1 C1 C2 F1 0.000(9) . .
C6 C1 C2 C3 0.000(11) . .
I1 C1 C2 C3 180.000(8) . .
C4 C3 C2 C1 0.000(10) . .
I2 C3 C2 C1 180.000(8) . .
C4 C3 C2 F1 180.000(7) . .
I2 C3 C2 F1 0.000(8) . .
F3 C5 C4 F2 0.000(10) . .
C6 C5 C4 F2 180.000(8) . .
F3 C5 C4 C3 180.000(9) . .
C6 C5 C4 C3 0.000(11) . .
C2 C3 C4 C5 0.000(11) . .
I2 C3 C4 C5 180.000(8) . .
C2 C3 C4 F2 180.000(7) . .
I2 C3 C4 F2 0.000(9) . .
C10 C9 C8 F5 180.000(4) . .
I4 C9 C8 F5 0.000(4) . .
C10 C9 C8 C7 0.000(6) . .
I4 C9 C8 C7 180.000(4) . .
C4 C5 C6 F4 180.000(7) . .
F3 C5 C6 F4 0.000(10) . .
C4 C5 C6 C1 0.000(11) . .
F3 C5 C6 C1 180.000(9) . .
C2 C1 C6 C5 0.000(11) . .
I1 C1 C6 C5 180.000(9) . .
C2 C1 C6 F4 180.000(7) . .
I1 C1 C6 F4 0.000(9) . .
C31 C30 N2 C30 55.9(16) . 4
N2 C30 C31 O2 -59.3(14) . .
F7 C11 C12 F8 0.000(6) . .
C10 C11 C12 F8 180.000(4) . .
F7 C11 C12 C7 180.000(6) . .
C10 C11 C12 C7 0.000(6) . .
C9 C8 C7 C12 0.000(6) . .
F5 C8 C7 C12 180.000(5) . .
C9 C8 C7 I3 180.000(4) . .
F5 C8 C7 I3 0.000(5) . .
F8 C12 C7 C8 180.000(6) . .
C11 C12 C7 C8 0.000(6) . .
F8 C12 C7 I3 0.000(6) . .
C11 C12 C7 I3 180.000(4) . .
C30 C31 O2 C31 60(2) . 4
