Bifurcated halogen bonds in the crystal structure of 2,2′-bi(1,8-naphthyridine)—1,4-diiodotetrafluorobenzene (1/1), C22H10F4I2N4
Wang, Yan; Xu, Shun; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 1207–1209; doi:10.1515/ncrs-2022-0427

data_8107335
_publ_section_title
;
 Bifurcated halogen bonds in the crystal structure of
 2,2&#x2032;-bi(1,8-naphthyridine)---1,4-diiodotetrafluorobenzene (1/1),
 C22H10F4I2N4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1207
_journal_page_last               1209
_journal_paper_doi               10.1515/ncrs-2022-0427
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C16 H10 N4, C6 F4 I2'
_chemical_formula_sum            'C22 H10 F4 I2 N4'
_chemical_formula_weight         660.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 101.673(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7940(3)
_cell_length_b                   5.34970(10)
_cell_length_c                   20.5119(5)
_cell_measurement_reflns_used    8574
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7900
_cell_measurement_theta_min      4.1730
_cell_volume                     1052.49(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      293(2)
_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 0.907
_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    -78.00  12.00   1.00    2.50    --  -13.80 -77.00  90.00   90
  2  \w    -41.00  54.00   1.00    2.50    --  -13.80  77.00-150.00   95
  3  \w    -66.00 -20.00   1.00    2.50    --  -13.80 122.00  11.39   46
  4  \w    -35.00   9.00   1.00    2.50    --  -13.80 -77.00-120.00   44
  5  \w     10.00  82.00   1.00    2.50    --   14.82  38.00-120.00   72
  6  \w    -20.00  54.00   1.00    2.50    --   14.82 -99.00-180.00   74
  7  \w     13.00  77.00   1.00    2.50    --   14.82  57.00   0.00   64
  8  \w    -41.00  42.00   1.00    2.50    --   14.82 -77.00 -30.00   83
  9  \w    -54.00  34.00   1.00    2.50    --   14.82 -38.00  60.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0148745000
_diffrn_orient_matrix_UB_12      0.0991404000
_diffrn_orient_matrix_UB_13      0.0204466000
_diffrn_orient_matrix_UB_21      0.0383232000
_diffrn_orient_matrix_UB_22      0.0834538000
_diffrn_orient_matrix_UB_23      -0.0163116000
_diffrn_orient_matrix_UB_31      -0.0614738000
_diffrn_orient_matrix_UB_32      0.0280601000
_diffrn_orient_matrix_UB_33      -0.0237206000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14098
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.521
_diffrn_reflns_theta_min         3.942
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.041
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0222
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0203P)^2^+0.4924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0505
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2214
_reflns_number_total             2416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0427_suppl.cif
_cod_data_source_block           w
_cod_database_code               8107335
_shelx_estimated_absorpt_t_max   0.529
_shelx_estimated_absorpt_t_min   0.494
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7)
;
_shelx_res_checksum              1475
_shelx_hkl_checksum              72921
_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 1.565
_oxdiff_exptl_absorpt_empirical_full_min 0.606