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_7158181
_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 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                 98.244(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.25520(10)
_cell_length_b                   15.3923(3)
_cell_length_c                   16.4781(3)
_cell_measurement_reflns_used    16617
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      33.5650
_cell_measurement_theta_min      2.4790
_cell_volume                     1319.13(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (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    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.899
_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     34.00  84.00   0.50   60.00    --   12.42  57.00 -60.00  100
  2  \w     -2.00  60.00   0.50   60.00    --   12.42  57.00 -90.00  124
  3  \w     -3.00  26.00   0.50   60.00    --   12.42  77.00  60.00   58
  4  \w     -2.00  79.00   0.50   60.00    --   12.42  57.00 150.00  162
  5  \w     15.00  52.00   0.50   60.00    --   12.42-112.00 123.00   74
  6  \w    -57.00  -7.00   0.50   60.00    --   12.42 -19.00 -30.00  100
  7  \w    -62.00   5.00   0.50   60.00    --   12.42 -19.00-150.00  134
  8  \w    -84.00   1.00   0.50   60.00    --  -12.58 -57.00 -60.00  170
  9  \w     50.00  75.00   0.50   60.00    --   12.42-178.00  30.00   50
 10  \w     40.00  83.00   0.50   60.00    --   12.42-178.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062624000
_diffrn_orient_matrix_UB_12      0.0112230000
_diffrn_orient_matrix_UB_13      -0.0419856000
_diffrn_orient_matrix_UB_21      0.1268740000
_diffrn_orient_matrix_UB_22      0.0168026000
_diffrn_orient_matrix_UB_23      0.0078779000
_diffrn_orient_matrix_UB_31      0.0496875000
_diffrn_orient_matrix_UB_32      -0.0414094000
_diffrn_orient_matrix_UB_33      -0.0081962000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25130
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.573
_diffrn_reflns_theta_min         2.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.024
_refine_diff_density_max         1.385
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.5979P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4037
_reflns_number_total             4674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           Bz-act-I-Form-2
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_database_code               7158181
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H10N4O4I1
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.554
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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), C3(H3), C5(H5), C6(H6), C14(H14), C18(H18), C15(H15), C16(H16),
 C17(H17)
;
_shelx_res_checksum              21407
_olex2_date_sample_data_collection 2021-04-22
_olex2_date_sample_submission    2021-01-12
_olex2_exptl_crystal_mounting_method 'mounted on a MiTegen loop'
_olex2_submission_original_sample_id 'Bz-act_1 (Form II)'
_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 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.713