Intermolecular binding preferences of haloethynyl halogen-bond donors as a function of molecular electrostatic potentials in a family of <i>N</i>-(pyridin-2-yl)amides.
Abeysekera, Amila M.; Averkiev, Boris B.; Le Magueres, Pierre; Aakeröy, Christer B; Organic & biomolecular chemistry 19 (2021) 6671–6681; doi:10.1039/d1ob01133b

data_7158177
_publ_section_title
;
 Intermolecular binding preferences of haloethynyl halogen-bond donors as
 a function of molecular electrostatic potentials in a family of
 <i>N</i>-(pyridin-2-yl)amides.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6671
_journal_page_last               6681
_journal_paper_doi               10.1039/d1ob01133b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C13 H8 I N3 O'
_chemical_formula_sum            'C13 H8 I N3 O'
_chemical_formula_weight         349.12
_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
_audit_creation_date             2021-04-26
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2021-06-10 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.558(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7284(3)
_cell_length_b                   6.7266(2)
_cell_length_c                   14.4741(4)
_cell_measurement_reflns_used    5522
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7750
_cell_measurement_theta_min      3.1550
_cell_volume                     1199.47(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     36.00  62.00   0.50    0.50    --   62.80   0.00-150.00   52
  2  \w     47.00  92.00   0.50    0.50    --   62.80  15.00-180.00   90
  3  \w     58.00  93.00   0.50    0.50    --   62.80  15.00 -30.00   70
  4  \w     43.00  85.00   0.50    0.50    --   62.80   0.00 -30.00   84
  5  \w     68.00  97.00   0.50    0.50    --   68.75  20.00  70.06   58
  6  \w     41.00  93.00   0.50    0.50    --   62.80  15.00 120.00  104
  7  \w     43.00  86.00   0.50    0.50    --   62.80   0.00  90.00   86
  8  \w    -71.00 -44.00   0.50    0.50    --  -35.00 -22.00 129.64   54
  9  \w    -60.00 -33.00   0.50    0.50    --  -33.58 -15.00   0.00   54
 10  \w    -65.00 -31.00   0.50    0.50    --  -35.00 -20.00 150.37   68
 11  \w    -72.00 -47.00   0.50    0.50    --  -35.00 -22.00 -67.14   50
 12  \w    -47.00 -22.00   0.50    0.50    --  -35.00 114.00  -7.76   50
 13  \w    -50.00 -25.00   0.50    0.50    --  -35.00 116.00  18.43   50
 14  \w    -52.00 -27.00   0.50    0.50    --  -35.00 121.00-158.39   50
 15  \w    -28.00  -2.00   0.50    0.50    --  -33.58  15.00-150.00   52
 16  \w    -26.00   2.00   0.50    0.50    --  -33.58  15.00-180.00   56
 17  \w    -39.00 -14.00   0.50    0.50    --  -33.58   0.00-180.00   50
 18  \w     32.00  67.00   0.50    0.50    --   62.80-125.00-180.00   70
 19  \w     40.00  66.00   0.50    0.50    --   62.80-125.00-150.00   52
 20  \w     51.00  78.00   0.50    0.50    --   62.80-125.00 -60.00   54
 21  \w     42.00  81.00   0.50    0.50    --   62.80-125.00-120.00   78
 22  \w     32.00  81.00   0.50    0.50    --   62.80-125.00 -90.00   98
 23  \w     32.00  68.00   0.50    0.50    --   62.80-125.00  30.00   72
 24  \w     53.00  89.00   0.50    0.50    --   68.75-126.00  57.99   72
 25  \w     38.00  64.00   0.50    0.50    --   62.80-125.00  90.00   52
 26  \w     35.00  69.00   0.50    0.50    --   68.75-133.00 142.78   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0362131000
_diffrn_orient_matrix_UB_12      -0.1275673000
_diffrn_orient_matrix_UB_13      -0.0749070000
_diffrn_orient_matrix_UB_21      0.1007565000
_diffrn_orient_matrix_UB_22      -0.0679851000
_diffrn_orient_matrix_UB_23      0.0768823000
_diffrn_orient_matrix_UB_31      -0.0645498000
_diffrn_orient_matrix_UB_32      -0.1776215000
_diffrn_orient_matrix_UB_33      0.0241877000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8148
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.057
_diffrn_reflns_theta_max         67.057
_diffrn_reflns_theta_min         3.588
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.908
_exptl_absorpt_correction_T_max  0.46137
_exptl_absorpt_correction_T_min  0.41004
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.83a (Rigaku Oxford Diffraction, 2020)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.041
_exptl_crystal_size_rad          0.030
_refine_diff_density_max         1.181
_refine_diff_density_min         -1.580
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0683P)^2^+0.7768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1957
_reflns_number_total             2136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           3act-I
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_database_code               7158177
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H8 I N3 O'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C14(H14), C6(H6), C16(H16), C3(H3), C18(H18), C5(H5), C17(H17)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.777
_oxdiff_exptl_absorpt_empirical_full_min 0.678