Halogen bonds in the crystal structure of 1,4-diiodotetrafluorobenzene–1,2-bis(4-pyridyl)propane (1/1), C19H14F4I2N2
Dang, Limin; Huang, Saijin; Yin, Aiwu; Zeitschrift für Kristallographie - New Crystal Structures 233 (2018) 473–475; doi:10.1515/ncrs-2017-0364

data_8106188
_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 f\"ur 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  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -80.00   4.00   1.00    6.63    --  -12.53 -57.00 -90.00   84
  2  \w    -20.00  26.00   1.00    6.63    --  -12.53 -99.00 150.00   46
  3  \w     -3.00  81.00   1.00    6.63    --   13.55  57.00 150.00   84
  4  \w     -3.00  81.00   1.00    6.63    --   13.55  57.00 -60.00   84
  5  \w     -3.00  81.00   1.00    6.63    --   13.55  57.00-150.00   84
  6  \w    -54.00  30.00   1.00    6.63    --   13.55 -57.00  30.00   84
  7  \w    -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       '\w 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/[\s^2^(Fo^2^)+(0.0250P)^2^+5.0060P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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