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_7158179
_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             2021-04-26
_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                 91.106(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.79810(10)
_cell_length_b                   11.5441(2)
_cell_length_c                   25.4972(4)
_cell_measurement_reflns_used    6074
_cell_measurement_temperature    100.00(18)
_cell_measurement_theta_max      76.2800
_cell_measurement_theta_min      3.4430
_cell_volume                     1117.73(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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(18)
_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 0.984
_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    -81.00 -28.00   0.50    2.91    --  -47.95 103.00 -73.00  106
  2  \w    -23.00   4.00   0.50    2.91    --  -47.95 103.00 -73.00   54
  3  \w    -47.00 -22.00   0.50   11.64    --  -86.25 103.00 -73.00   50
  4  \w    -21.00  28.00   0.50    2.91    --  -47.95  19.00-150.00   98
  5  \w     25.00  50.00   0.50    2.91    --   47.95-103.00-174.00   50
  6  \w     80.00 106.00   0.50   11.64    --  107.75-103.00-174.00   52
  7  \w     67.00  98.00   0.50   11.64    --  107.75 -77.00 -90.00   62
  8  \w     76.00 108.00   0.50   11.64    --  107.75-125.00 -60.00   64
  9  \w     40.00  70.00   0.50   11.64    --  107.75 -61.00  60.00   60
 10  \w     43.00  69.00   0.50   11.64    --  107.75 -61.00  30.00   52
 11  \w     41.00  70.00   0.50   11.64    --  107.75 -61.00 -30.00   58
 12  \w     36.00  69.00   0.50   11.64    --  107.75 -61.00 -90.00   66
 13  \w     35.00  60.00   0.50   11.64    --  107.75 -61.00 -60.00   50
 14  \w     35.00  66.00   0.50   11.64    --  107.75 -77.00-120.00   62
 15  \w     36.00 103.00   0.50   11.64    --  107.75 -94.00-150.00  134
 16  \w     72.00  98.00   0.50   11.64    --  107.75 -94.00-180.00   52
 17  \w     37.00  62.00   0.50   11.64    --  107.75-125.00 -60.00   50
 18  \w     42.00  68.00   0.50   11.64    --  107.75-125.00   0.00   52
 19  \w     38.00  71.00   0.50   11.64    --  107.75 -61.00   0.00   66
 20  \w     94.00 149.00   0.50   11.64    --  107.75  15.00  30.00  110
 21  \w    107.00 156.00   0.50   11.64    --  107.75 103.00 -73.00   98
 22  \w    144.00 177.00   0.50   11.64    --  107.75  61.00-150.00   66
 23  \w    147.00 172.00   0.50   11.64    --  107.75 125.00-150.00   50
 24  \w    111.00 141.00   0.50   11.64    --  107.75  61.00-150.00   60
 25  \w    102.00 128.00   0.50   11.64    --  107.75 125.00-150.00   52
 26  \w    131.00 156.00   0.50   11.64    --  107.75 125.00  60.00   50
 27  \w     43.00  69.00   0.50   11.64    --  107.75 -61.00 120.00   52
 28  \w     35.00  61.00   0.50   11.64    --  107.75 -77.00 -90.00   52
 29  \w     35.00  61.00   0.50   11.64    --  107.75 -77.00-180.00   52
 30  \w   -118.00 -73.00   0.50    2.91    --  -47.95-125.00   0.00   90
 31  \w   -111.00 -75.00   0.50    2.91    --  -47.95-125.00  60.00   72
 32  \w   -112.00 -79.00   0.50    2.91    --  -47.95-125.00-120.00   66
 33  \w   -104.00 -77.00   0.50   11.64    --  -86.25 -45.00-150.00   54
 34  \w   -129.00-104.00   0.50   11.64    --  -86.25-103.00-174.00   50
 35  \w   -157.00-131.00   0.50   11.64    --  -86.25 -45.00-150.00   52
;
_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      0.2585123000
_diffrn_orient_matrix_UB_12      -0.0717099000
_diffrn_orient_matrix_UB_13      -0.0326273000
_diffrn_orient_matrix_UB_21      -0.0685948000
_diffrn_orient_matrix_UB_22      -0.1063516000
_diffrn_orient_matrix_UB_23      0.0348326000
_diffrn_orient_matrix_UB_31      -0.3051028000
_diffrn_orient_matrix_UB_32      -0.0368238000
_diffrn_orient_matrix_UB_33      -0.0370603000
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8420
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.261
_diffrn_reflns_theta_min         3.467
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62229
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method 'recrystallized from acetone'
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0585P)^2^+0.6051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2199
_reflns_number_total             2342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           2act-Cl
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_database_code               7158179
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H8 Cl1 N3 O1'
_chemical_oxdiff_usercomment     'Sample from exp_40 but different cell'
_shelx_estimated_absorpt_t_max   0.660
_shelx_estimated_absorpt_t_min   0.310
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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), C6(H6), C18(H18), C5(H5), C17(H17), C16(H16), C15(H15)
;
_shelx_res_checksum              63065
_olex2_date_sample_data_collection 2021-01-13
_olex2_date_sample_submission    2021-01-12
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_olex2_submission_original_sample_id 2act-Cl
_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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.520