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_7158180
_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         'C14 H9 I N2 O'
_chemical_formula_sum            'C14 H9 I N2 O'
_chemical_formula_weight         348.13
_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                 95.784(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.08450(10)
_cell_length_b                   16.1979(4)
_cell_length_c                   19.1245(4)
_cell_measurement_reflns_used    5198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.8110
_cell_measurement_theta_min      3.5680
_cell_volume                     1258.84(5)
_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 0.991
_diffrn_measured_fraction_theta_max 0.955
_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    -28.00  -3.00   0.50    5.00    --  -35.00  15.00-150.00   50
  2  \w     39.00  79.00   0.50    5.00    --   61.20-125.00 -90.00   80
  3  \w     45.00  71.00   0.50    5.00    --   61.20-125.00-150.00   52
  4  \w     44.00  70.00   0.50    5.00    --   61.20  15.00 150.00   52
  5  \w     36.00  64.00   0.50    5.00    --   61.20-125.00 -30.00   56
  6  \w     78.00 103.00   0.50    5.00    --   61.20  15.00 150.00   50
  7  \w     55.00  93.00   0.50    5.00    --   70.01-125.00 -90.00   76
  8  \w     79.00 113.00   0.50    5.00    --   70.01  15.00 -90.00   68
  9  \w     67.00  95.00   0.50    5.00    --   74.10-119.00-154.00   56
 10  \w     73.00 107.00   0.50    5.00    --   74.10   0.00-180.00   68
 11  \w     41.00  66.00   0.50    5.00    --   74.10   0.00-180.00   50
 12  \w     89.00 115.00   0.50    5.00    --   74.10  15.00-120.00   52
 13  \w     32.00  76.00   0.50    5.00    --   74.10-125.00   0.00   88
 14  \w     39.00 100.00   0.50    5.00    --   74.10-125.00 -60.00  122
 15  \w    -18.00   8.00   0.50    5.00    --  -34.26  15.00 -60.00   52
 16  \w    -28.00  -3.00   0.50    5.00    --  -35.00  15.00 -90.00   50
 17  \w     34.00  66.00   0.50    5.00    --   61.20  15.00-120.00   64
 18  \w     69.00 104.00   0.50    5.00    --   61.20  15.00-120.00   70
 19  \w     57.00  91.00   0.50    5.00    --   74.10  15.00-120.00   68
 20  \w     38.00  68.00   0.50    5.00    --   74.10-125.00-120.00   60
 21  \w     74.00 100.00   0.50    5.00    --   74.10-125.00-120.00   52
 22  \w     34.00  60.00   0.50    5.00    --   74.10-125.00 -30.00   52
 23  \w    -69.00 -28.00   0.50    5.00    --  -35.00 -15.00 -90.00   82
 24  \w     57.00  83.00   0.50    5.00    --   61.20-125.00  30.00   52
 25  \w     73.00  99.00   0.50    5.00    --   74.10-125.00   0.00   52
;
_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      0.3404394000
_diffrn_orient_matrix_UB_12      0.0361184000
_diffrn_orient_matrix_UB_13      -0.0105246000
_diffrn_orient_matrix_UB_21      -0.1512551000
_diffrn_orient_matrix_UB_22      0.0871529000
_diffrn_orient_matrix_UB_23      -0.0066730000
_diffrn_orient_matrix_UB_31      0.0708302000
_diffrn_orient_matrix_UB_32      0.0120492000
_diffrn_orient_matrix_UB_33      0.0799816000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8164
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.202
_diffrn_reflns_theta_min         3.584
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.896
_exptl_absorpt_correction_T_max  0.838
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.83a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.837
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.043
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.022
_refine_diff_density_max         1.077
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0250P)^2^+5.8103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2183
_reflns_number_total             2361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           Bz-act-I-Form-1
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_database_code               7158180
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H9 I N2 O'
_shelx_estimated_absorpt_t_max   0.669
_shelx_estimated_absorpt_t_min   0.482
_reflns_odcompleteness_completeness 99.31
_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), C6(H6), C3(H3), C5(H5), C14(H14), C18(H18), C17(H17), C16(H16),
 C15(H15)
;
_shelx_res_checksum              75708
_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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.832