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_7158173
_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 Cl N2 O'
_chemical_formula_sum            'C14 H9 Cl N2 O'
_chemical_formula_weight         256.68
_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   difmap
_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                 99.571(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.10890(10)
_cell_length_b                   22.0087(4)
_cell_length_c                   10.5605(2)
_cell_measurement_reflns_used    6026
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1920
_cell_measurement_theta_min      4.6920
_cell_volume                     1170.90(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.76a (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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.920
_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     29.00  69.00   0.50    1.60    --  101.80 -61.00  30.00   80
  2  \w     29.00  69.00   0.50    1.60    --  101.80 -61.00  60.00   80
  3  \w     29.00  69.00   0.50    1.60    --  101.80 -61.00 120.00   80
  4  \w     29.00  69.00   0.50    1.60    --  101.80 -61.00 -90.00   80
  5  \w     29.00  69.00   0.50    1.60    --  101.80 -61.00-120.00   80
  6  \w    122.00 174.00   0.50    1.60    --  101.80  45.00-150.00  104
  7  \w     30.00 118.00   0.50    0.40    --   45.89  60.00 135.00  176
  8  \w    -28.00  30.00   0.50    0.40    --  -45.89  19.00 120.00  116
  9  \w    -44.00  27.00   0.50    0.40    --  -45.89  37.00  90.00  142
 10  \w    -53.00 -20.00   0.50    1.60    --  -91.75  45.00  60.00   66
 11  \w    -53.00 -20.00   0.50    1.60    --  -91.75  45.00  30.00   66
 12  \w    -68.00   0.00   0.50    0.40    --  -45.89  77.00-150.00  136
 13  \w    -53.00 -20.00   0.50    1.60    --  -91.75  45.00-150.00   66
 14  \w    -53.00 -20.00   0.50    1.60    --  -91.75  45.00-120.00   66
 15  \w   -163.00-122.00   0.50    1.60    --  -91.75 -45.00 -60.00   82
 16  \w   -163.00-127.00   0.50    1.60    --  -91.75 -61.00 -90.00   72
 17  \w   -163.00-126.00   0.50    1.60    --  -91.75 -77.00 -30.00   74
 18  \w   -163.00-127.00   0.50    1.60    --  -91.75 -61.00-120.00   72
 19  \w   -163.00-127.00   0.50    1.60    --  -91.75 -61.00 -30.00   72
 20  \w    -82.00 -29.00   0.50    0.40    --  -45.89 125.00 120.00  106
 21  \w   -163.00-127.00   0.50    1.60    --  -91.75 -61.00  90.00   72
 22  \w   -163.00-126.00   0.50    1.60    --  -91.75 -77.00  60.00   74
 23  \w   -163.00-122.00   0.50    1.60    --  -91.75 -45.00   0.00   82
 24  \w   -163.00-121.00   0.50    1.60    --  -91.75 -94.00 120.00   84
;
_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      0.2911374000
_diffrn_orient_matrix_UB_12      0.0205352000
_diffrn_orient_matrix_UB_13      0.0111693000
_diffrn_orient_matrix_UB_21      -0.0401649000
_diffrn_orient_matrix_UB_22      0.0448920000
_diffrn_orient_matrix_UB_23      0.1070078000
_diffrn_orient_matrix_UB_31      0.0844749000
_diffrn_orient_matrix_UB_32      -0.0496389000
_diffrn_orient_matrix_UB_33      0.1015227000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8652
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.387
_diffrn_reflns_theta_min         4.017
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.76a (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    1.456
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.4354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2101
_reflns_number_total             2241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           Bz-act-Cl
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_database_code               7158173
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H9 N2 O Cl'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_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 1.182
_oxdiff_exptl_absorpt_empirical_full_min 0.844