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_7158178
_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
_chemical_name_systematic        3act-Cl
_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                 93.485(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.84600(10)
_cell_length_b                   9.8013(2)
_cell_length_c                   29.8606(6)
_cell_measurement_reflns_used    10206
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.8990
_cell_measurement_theta_min      2.9640
_cell_volume                     1123.54(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      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.969
_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    -64.00 -39.00   0.50    5.43    --  -47.95 -38.00 -90.00   50
  2  \w   -108.00 -76.00   0.50    5.43    --  -47.95 -38.00 -90.00   64
  3  \w   -117.00 -76.00   0.50    5.43    --  -47.95-125.00   0.00   82
  4  \w   -103.00 -76.00   0.50    5.43    --  -47.95-124.00  76.00   54
  5  \w    -51.00 -14.00   0.50   21.73    --  -86.25  45.00-150.00   74
  6  \w    -89.00 -63.00   0.50   21.73    --  -86.25 148.00 -39.00   52
  7  \w   -100.00 -65.00   0.50    5.43    --  -47.95 148.00 -39.00   70
  8  \w    -50.00 -17.00   0.50   21.73    --  -86.25  45.00  90.00   66
  9  \w    -63.00 -38.00   0.50    5.43    --  -47.95 124.00 155.00   50
 10  \w    -62.00 -36.00   0.50   21.73    --  -86.25 124.00 155.00   52
 11  \w   -147.00 -73.00   0.50   21.73    --  -86.25 -45.00 120.00  148
 12  \w   -119.00 -89.00   0.50   21.73    --  -86.25-124.00  76.00   60
 13  \w    -98.00 -73.00   0.50    5.43    --  -47.95-125.00  90.00   50
 14  \w   -102.00 -62.00   0.50    5.43    --  -47.95-148.00 -87.00   80
 15  \w   -127.00-102.00   0.50   21.73    --  -86.25-148.00 -87.00   50
 16  \w     36.00  95.00   0.50    5.43    --   47.95-124.00  76.00  118
 17  \w     49.00  74.00   0.50   21.73    --  107.75-124.00  76.00   50
 18  \w     73.00  99.00   0.50   21.73    --  107.75 -94.00 120.00   52
 19  \w     44.00  70.00   0.50   21.73    --  107.75 -61.00  90.00   52
 20  \w     36.00  61.00   0.50   21.73    --  107.75 -61.00  30.00   50
 21  \w     46.00 102.00   0.50   21.73    --  107.75 -77.00   0.00  112
 22  \w     80.00 105.00   0.50   21.73    --  107.75 -77.00 -60.00   50
 23  \w     77.00 107.00   0.50   21.73    --  107.75-106.00 -74.59   60
 24  \w     63.00  88.00   0.50   21.73    --  107.75-148.00 -87.00   50
 25  \w     57.00  84.00   0.50   21.73    --  107.75-125.00 -90.00   54
 26  \w     67.00 112.00   0.50   21.73    --  107.75-125.00-150.00   90
 27  \w     54.00  80.00   0.50    5.43    --   47.95-148.00 -87.00   52
 28  \w     36.00  69.00   0.50   21.73    --  107.75 -61.00-120.00   66
 29  \w     52.00  93.00   0.50   21.73    --  107.75 -77.00-150.00   82
 30  \w     47.00 106.00   0.50   21.73    --  107.75 -94.00 -90.00  118
 31  \w     87.00 112.00   0.50   21.73    --  107.75-125.00   0.00   50
 32  \w     42.00  69.00   0.50   21.73    --  107.75 -77.00 -60.00   54
 33  \w     41.00  67.00   0.50   21.73    --  107.75 -61.00 -60.00   52
 34  \w     35.00  60.00   0.50   21.73    --  107.75 -61.00 -30.00   50
 35  \w     35.00  69.00   0.50   21.73    --  107.75 -61.00 -90.00   68
 36  \w     94.00 167.00   0.50   21.73    --  107.75  15.00 -90.00  146
 37  \w    110.00 178.00   0.50   21.73    --  107.75  15.00 -30.00  136
 38  \w    103.00 156.00   0.50   21.73    --  107.75  30.00 120.00  106
 39  \w    144.00 178.00   0.50   21.73    --  107.75  61.00 150.00   68
 40  \w    122.00 147.00   0.50   21.73    --  107.75 124.00 155.00   50
 41  \w    100.00 139.00   0.50   21.73    --  107.75  61.00 150.00   78
 42  \w     80.00 117.50   0.50   21.73    --  107.75 148.00 -39.00   75
;
_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      -0.1510452000
_diffrn_orient_matrix_UB_12      -0.1301535000
_diffrn_orient_matrix_UB_13      -0.0226384000
_diffrn_orient_matrix_UB_21      -0.0811971000
_diffrn_orient_matrix_UB_22      -0.0572895000
_diffrn_orient_matrix_UB_23      0.0462612000
_diffrn_orient_matrix_UB_31      -0.3627840000
_diffrn_orient_matrix_UB_32      0.0669608000
_diffrn_orient_matrix_UB_33      -0.0044030000
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            11353
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.222
_diffrn_reflns_theta_min         2.965
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64902
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method
'recrystallized from touluene, ACN, and ethylacetate'
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0622P)^2^+1.2212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2235
_reflns_number_total             2305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           3act-Cl
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_database_code               7158178
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H18 N3 O Cl'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.746
_reflns_odcompleteness_completeness 98.56
_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), C18(H18), C17(H17), C14(H14), C16(H16), C3(H3), C6(H6), C5(H5)
;
_shelx_res_checksum              18269
_olex2_date_sample_data_collection 2020-12-15
_olex2_date_sample_submission    2020-12-14
_olex2_exptl_crystal_mounting_method 'mounted on a glass fibre'
_olex2_submission_original_sample_id 3-act-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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.510