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_7158183
_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 Br N3 O'
_chemical_formula_sum            'C13 H8 Br N3 O'
_chemical_formula_weight         302.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                112.512(2)
_cell_angle_beta                 93.859(2)
_cell_angle_gamma                97.720(2)
_cell_formula_units_Z            2
_cell_length_a                   6.75090(10)
_cell_length_b                   9.2249(2)
_cell_length_c                   10.2422(2)
_cell_measurement_reflns_used    7400
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.3840
_cell_measurement_theta_min      4.7130
_cell_volume                     578.97(2)
_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 2018/2 (Sheldrick, 2018)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.951
_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    -61.00  15.00   0.50    0.05    --  -45.89  57.00-120.00  152
  2  \w     33.00 118.00   0.50    0.05    --   45.89  46.00 -39.00  170
  3  \w     33.00  64.00   0.50    0.05    --   45.89  31.00  99.80   62
  4  \w    -28.00  30.00   0.50    0.05    --  -45.89  19.00  30.00  116
  5  \w    -28.00  30.00   0.50    0.05    --  -45.89  19.00   0.00  116
  6  \w    -28.00  30.00   0.50    0.05    --  -45.89  19.00 -90.00  116
  7  \w     33.00 121.00   0.50    0.05    --   45.89  19.00  90.00  176
  8  \w    -28.00  30.00   0.50    0.05    --  -45.89  19.00 150.00  116
  9  \w    -64.00 -33.00   0.50    0.05    --  -45.89 -31.00  49.50   62
 10  \w   -118.00 -33.00   0.50    0.05    --  -45.89 -46.00 171.00  170
 11  \w   -108.00 -19.00   0.50    0.20    --  -91.75  77.00   0.00  178
 12  \w    -54.00 -19.00   0.50    0.20    --  -91.75  46.00 -39.00   70
 13  \w    -64.00 -33.00   0.50    0.05    --  -45.89 -31.00-172.18   62
 14  \w     29.00  69.00   0.50    0.20    --  101.80 -61.00-180.00   80
 15  \w     29.00  69.00   0.50    0.20    --  101.80 -61.00  30.00   80
 16  \w     29.00  69.00   0.50    0.20    --  101.80 -61.00  60.00   80
 17  \w     29.00 104.00   0.50    0.20    --  101.80 -77.00 150.00  150
 18  \w     29.00  69.00   0.50    0.20    --  101.80 -61.00 -30.00   80
 19  \w     29.00 104.00   0.50    0.20    --  101.80 -94.00 -60.00  150
 20  \w     36.00 108.00   0.50    0.20    --  101.80-125.00-180.00  144
 21  \w     36.00 108.00   0.50    0.20    --  101.80-125.00 -90.00  144
 22  \w     29.00 104.00   0.50    0.20    --  101.80 -94.00-180.00  150
 23  \w     36.00 108.00   0.50    0.20    --  101.80-125.00 -60.00  144
 24  \w     29.00 104.00   0.50    0.20    --  101.80 -94.00   0.00  150
 25  \w     29.00 104.00   0.50    0.20    --  101.80 -94.00  60.00  150
 26  \w     36.00 108.00   0.50    0.20    --  101.80-125.00 150.00  144
 27  \w   -166.00 -79.00   0.50    0.20    --  -91.75 -29.00-133.85  174
 28  \w   -163.00-126.00   0.50    0.20    --  -91.75 -77.00-120.00   74
 29  \w   -163.00-126.00   0.50    0.20    --  -91.75 -77.00 -90.00   74
 30  \w   -163.00-126.00   0.50    0.20    --  -91.75 -77.00 -30.00   74
 31  \w   -163.00-127.00   0.50    0.20    --  -91.75 -61.00  30.00   72
 32  \w   -166.00 -88.00   0.50    0.20    --  -91.75 -30.00 150.00  156
 33  \w   -163.00-122.00   0.50    0.20    --  -91.75 -45.00   0.00   82
 34  \w   -163.00-122.00   0.50    0.20    --  -91.75 -45.00 -60.00   82
 35  \w   -163.00-122.00   0.50    0.20    --  -91.75 -45.00 -90.00   82
 36  \w   -163.00-121.00   0.50    0.20    --  -91.75 -94.00-180.00   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      -0.0694677000
_diffrn_orient_matrix_UB_12      -0.1431762000
_diffrn_orient_matrix_UB_13      0.0382985000
_diffrn_orient_matrix_UB_21      0.2082596000
_diffrn_orient_matrix_UB_22      0.0283165000
_diffrn_orient_matrix_UB_23      0.0855826000
_diffrn_orient_matrix_UB_31      -0.0757834000
_diffrn_orient_matrix_UB_32      0.1113365000
_diffrn_orient_matrix_UB_33      0.1348078000
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8710
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.953
_diffrn_reflns_theta_min         4.713
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82297
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_description       irregular
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0244
_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^)+(0.0345P)^2^+0.5745P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2241
_reflns_number_total             2274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           4act-Br
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_database_code               7158183
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H8 Br N3 O'
_reflns_odcompleteness_completeness 99.95
_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), C5(H5), C18(H18), C6(H6), C17(H17), C14(H14), C15(H15), C3(H3)
;
_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.735