#------------------------------------------------------------------------------
#$Date: 2022-11-21 12:08:51 +0200 (Mon, 21 Nov 2022) $
#$Revision: 279436 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106188.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_8106188
loop_
_publ_author_name
'Dang, Limin'
'Huang, Saijin'
'Yin, Aiwu'
_publ_section_title
;
 Halogen bonds in the crystal structure of
 1,4-diiodotetrafluorobenzene--1,2-bis(4-pyridyl)propane (1/1),
 C19H14F4I2N2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              473
_journal_page_last               475
_journal_paper_doi               10.1515/ncrs-2017-0364
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C3 F2 I, C6.5 H7 N'
_chemical_formula_sum            'C9.5 H7 F2 I N'
_chemical_formula_weight         300.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 113.532(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.997(2)
_cell_length_b                   4.4785(3)
_cell_length_c                   23.242(3)
_cell_measurement_reflns_used    4386
_cell_measurement_temperature    287
_cell_measurement_theta_max      27.1190
_cell_measurement_theta_min      4.2360
_cell_volume                     2003.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      287
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -80.00   4.00   1.00    6.63    --  -12.53 -57.00 -90.00   84
  2  ω    -20.00  26.00   1.00    6.63    --  -12.53 -99.00 150.00   46
  3  ω     -3.00  81.00   1.00    6.63    --   13.55  57.00 150.00   84
  4  ω     -3.00  81.00   1.00    6.63    --   13.55  57.00 -60.00   84
  5  ω     -3.00  81.00   1.00    6.63    --   13.55  57.00-150.00   84
  6  ω    -54.00  30.00   1.00    6.63    --   13.55 -57.00  30.00   84
  7  ω    -56.00  14.00   1.00    6.63    --   13.55 -38.00-180.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065394000
_diffrn_orient_matrix_UB_12      -0.0238660000
_diffrn_orient_matrix_UB_13      -0.0273194000
_diffrn_orient_matrix_UB_21      0.0354288000
_diffrn_orient_matrix_UB_22      0.0377535000
_diffrn_orient_matrix_UB_23      0.0170520000
_diffrn_orient_matrix_UB_31      0.0077730000
_diffrn_orient_matrix_UB_32      -0.1519289000
_diffrn_orient_matrix_UB_33      0.0085186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9761
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         3.372
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0324
_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)+(0.0250P)²+5.0060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0706
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1690
_reflns_number_total             1857
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0364_suppl.cif
_cod_data_source_block           w
_cod_original_formula_sum        'C9.50 H7 F2 I N'
_cod_database_code               8106188
_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.
;
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.439
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.326
_oxdiff_exptl_absorpt_empirical_full_min 0.605
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.41548(2) 0.26813(6) 0.34547(2) 0.05142(13) Uani 1 1 d . . . . .
F1 F 0.54774(14) -0.1618(7) 0.41246(12) 0.0685(8) Uani 1 1 d . . . . .
F2 F 0.61004(14) -0.3697(7) 0.52822(13) 0.0752(8) Uani 1 1 d . . . . .
C1 C 0.4665(2) 0.1077(9) 0.43808(18) 0.0424(9) Uani 1 1 d . . . . .
C2 C 0.5227(2) -0.0791(9) 0.45520(19) 0.0444(10) Uani 1 1 d . . . . .
C3 C 0.5556(2) -0.1833(9) 0.5155(2) 0.0481(10) Uani 1 1 d . . . . .
N1 N 0.3545(2) 0.5169(8) 0.22681(16) 0.0561(9) Uani 1 1 d . . . . .
C4 C 0.2877(2) 0.5791(11) 0.1968(2) 0.0544(11) Uani 1 1 d . . . . .
H4 H 0.2568 0.5018 0.2126 0.065 Uiso 1 1 calc R . . . .
C5 C 0.2614(2) 0.7514(9) 0.1435(2) 0.0501(11) Uani 1 1 d . . . . .
H5 H 0.2139 0.7879 0.1245 0.060 Uiso 1 1 calc R . . . .
C6 C 0.3051(2) 0.8710(8) 0.11813(17) 0.0382(9) Uani 1 1 d . . . . .
C7 C 0.3746(2) 0.8034(10) 0.1494(2) 0.0532(11) Uani 1 1 d . . . . .
H7 H 0.4067 0.8764 0.1347 0.064 Uiso 1 1 calc R . . . .
C8 C 0.3963(2) 0.6293(12) 0.2022(2) 0.0636(13) Uani 1 1 d . . . . .
H8 H 0.4435 0.5871 0.2220 0.076 Uiso 1 1 calc R . . . .
C9 C 0.2786(2) 1.0550(8) 0.05967(16) 0.0411(9) Uani 1 1 d . . . . .
H9A H 0.3161 1.1791 0.0587 0.049 Uiso 1 1 calc R . . . .
H9B H 0.2422 1.1861 0.0605 0.049 Uiso 1 1 calc R . . . .
C10 C 0.2500 0.8656(12) 0.0000 0.0432(13) Uani 1 2 d S T P . .
H10A H 0.2133 0.7381 0.0014 0.052 Uiso 0.5 1 calc R . . . .
H10B H 0.2867 0.7381 -0.0014 0.052 Uiso 0.5 1 calc R . . . .
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'
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'
N N 0.0061 0.0033 '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
C2 C1 I1 122.1(3) . .
C2 C1 C3 116.3(4) . 5_656
C3 C1 I1 121.5(3) 5_656 .
F1 C2 C1 119.9(4) . .
F1 C2 C3 118.3(3) . .
C1 C2 C3 121.8(4) . .
F2 C3 C1 120.1(4) . 5_656
F2 C3 C2 118.0(4) . .
C2 C3 C1 121.9(4) . 5_656
C4 N1 C8 116.0(4) . .
N1 C4 H4 118.2 . .
N1 C4 C5 123.7(4) . .
C5 C4 H4 118.2 . .
C4 C5 H5 119.8 . .
C4 C5 C6 120.4(4) . .
C6 C5 H5 119.8 . .
C5 C6 C9 122.2(4) . .
C7 C6 C5 115.7(4) . .
C7 C6 C9 122.1(4) . .
C6 C7 H7 119.9 . .
C8 C7 C6 120.1(4) . .
C8 C7 H7 119.9 . .
N1 C8 C7 124.2(4) . .
N1 C8 H8 117.9 . .
C7 C8 H8 117.9 . .
C6 C9 H9A 109.0 . .
C6 C9 H9B 109.0 . .
C6 C9 C10 112.8(3) . .
H9A C9 H9B 107.8 . .
C10 C9 H9A 109.0 . .
C10 C9 H9B 109.0 . .
C9 C10 C9 112.6(4) . 2
C9 C10 H10A 109.1 2 .
C9 C10 H10A 109.1 . .
C9 C10 H10B 109.1 2 .
C9 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.111(4) .
F1 C2 1.348(4) .
F2 C3 1.350(5) .
C1 C2 1.370(5) .
C1 C3 1.375(6) 5_656
C2 C3 1.374(6) .
C3 C1 1.375(6) 5_656
N1 C4 1.323(5) .
N1 C8 1.325(6) .
C4 H4 0.9300 .
C4 C5 1.373(6) .
C5 H5 0.9300 .
C5 C6 1.381(6) .
C6 C7 1.380(6) .
C6 C9 1.494(5) .
C7 H7 0.9300 .
C7 C8 1.368(6) .
C8 H8 0.9300 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.529(5) .
C10 C9 1.529(5) 2
C10 H10A 0.9700 .
C10 H10B 0.9700 .
