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_7158176
_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 Cl N3 O'
_chemical_formula_sum            'C13 H8 Cl N3 O'
_chemical_formula_weight         257.67
_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             2021-03-03
_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                 90.876(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.77350(10)
_cell_length_b                   10.1396(2)
_cell_length_c                   29.0994(6)
_cell_measurement_reflns_used    4423
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2880
_cell_measurement_theta_min      3.0390
_cell_volume                     1113.26(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.80a (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 0.992
_diffrn_measured_fraction_theta_max 0.922
_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    116.00 160.00   0.50    2.40    --  104.42 101.00 -40.00   88
  2  \w     42.00  68.00   0.50    2.40    --  104.42 -61.00 -90.00   52
  3  \w     37.00  65.00   0.50    2.40    --  104.42 -77.00-150.00   56
  4  \w     71.00  97.00   0.50    2.40    --  104.42 -77.00-150.00   52
  5  \w     -2.00  23.00   0.50    0.60    --  -46.02  19.00-120.00   50
  6  \w    -49.00 -20.00   0.50    2.40    --  -91.75  45.00 -90.00   58
  7  \w    -10.00  15.00   0.50    0.60    --  -46.02  19.00 -30.00   50
  8  \w    -49.00 -20.00   0.50    2.40    --  -91.75  45.00  90.00   58
  9  \w    -81.00 -19.00   0.50    2.40    --  -91.75 112.00  47.00  124
 10  \w   -166.00 -79.00   0.50    2.40    --  -91.75 -27.00  40.00  174
 11  \w   -110.00 -44.00   0.50    0.60    --  -46.02 -27.00  40.00  132
 12  \w    -71.00 -40.00   0.50    2.40    --  -91.75 101.00 -40.00   62
 13  \w    -68.00 -35.00   0.50    0.60    --  -46.02 125.00   0.00   66
 14  \w     59.00  85.00   0.50    0.60    --   46.02-125.00 120.00   52
 15  \w   -146.00-106.00   0.50    2.40    --  -91.75-101.00-144.00   80
 16  \w    -53.00 -28.00   0.50    2.40    --  -91.75  45.00 -60.00   50
 17  \w    109.00 136.00   0.50    2.40    --  101.80 125.00  60.00   54
 18  \w     29.00  54.00   0.50    2.40    --  101.80 -61.00-150.00   50
 19  \w     82.00 108.00   0.50    2.40    --  101.80-125.00-120.00   52
 20  \w    136.00 162.00   0.50    2.40    --  101.80  61.00-150.00   52
 21  \w    142.00 168.00   0.50    2.40    --  101.80 125.00  60.00   52
 22  \w     33.00  63.00   0.50    2.40    --  101.80 -61.00   0.00   60
 23  \w     33.00 107.00   0.50    0.60    --   46.02  19.00 -60.00  148
;
_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      -0.0773164000
_diffrn_orient_matrix_UB_12      -0.0058335000
_diffrn_orient_matrix_UB_13      -0.0521027000
_diffrn_orient_matrix_UB_21      0.1229322000
_diffrn_orient_matrix_UB_22      -0.1448497000
_diffrn_orient_matrix_UB_23      -0.0008797000
_diffrn_orient_matrix_UB_31      -0.3815970000
_diffrn_orient_matrix_UB_32      -0.0454399000
_diffrn_orient_matrix_UB_33      0.0094145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            3178
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.514
_diffrn_reflns_theta_min         3.038
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.960
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.80a (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    1.537
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.6193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2965
_reflns_number_total             3178
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9769\% 
around [-0.00 0.00 1.00] (reciprocal) or [0.12 -0.00 0.99] (direct)
;
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           4act-Cl
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_database_code               7158176
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.66(4)
 0.130(7) 0.21(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C14(H14), C15(H15), C3(H3), C6(H6), C5(H5), C18(H18), 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 1.202
_oxdiff_exptl_absorpt_empirical_full_min 0.798
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2