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_7158174
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 95.148(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8797(2)
_cell_length_b                   21.3190(14)
_cell_length_c                   14.8922(9)
_cell_measurement_reflns_used    4602
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      75.0960
_cell_measurement_theta_min      3.5950
_cell_volume                     1226.78(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_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      180.00(10)
_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 0.981
_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  30.00   0.50    3.95    --  -43.30  59.00  44.00  182
  2  \w    -68.00 -21.00   0.50    3.95    --  -43.30 -59.00 -95.00   94
  3  \w   -111.00 -86.00   0.50    3.95    --  -43.30 -59.00 -95.00   50
  4  \w   -163.00-134.00   0.50   15.82    --  -90.25 -59.00 -95.00   58
  5  \w    -66.00 -41.00   0.50   15.82    --  -90.25  59.00  44.00   50
  6  \w     38.00  63.00   0.50   15.82    --  111.75 -59.00 -95.00   50
  7  \w    114.00 178.00   0.50   15.82    --  111.75  59.00  44.00  128
  8  \w    -84.00 -48.00   0.50    3.95    --  -43.30 125.00 150.00   72
  9  \w    -45.00 -14.00   0.50    3.95    --  -43.30 125.00 150.00   62
 10  \w     67.00 107.00   0.50    3.95    --   43.30  59.00  44.00   80
 11  \w    -51.00 -26.00   0.50   15.82    --  -90.25  45.00-180.00   50
 12  \w    -50.00 -24.00   0.50   15.82    --  -90.25  45.00-150.00   52
 13  \w     38.00  64.00   0.50   15.82    --  111.75 -61.00 -30.00   52
 14  \w     42.00  71.00   0.50   15.82    --  111.75 -61.00 120.00   58
 15  \w     92.00 133.00   0.50   15.82    --  111.75  45.00 -30.00   82
 16  \w     42.00  70.00   0.50   15.82    --  111.75 -94.00 -90.00   56
 17  \w     39.00  93.00   0.50   15.82    --  111.75-125.00 120.00  108
 18  \w     74.00  99.00   0.50   15.82    --  111.75 -94.00 -90.00   50
 19  \w     48.00 104.00   0.50   15.82    --  111.75 -77.00   0.00  112
 20  \w     43.00  71.00   0.50   15.82    --  111.75 -61.00 150.00   56
 21  \w     45.00  70.00   0.50   15.82    --  111.75 -61.00 -60.00   50
 22  \w     39.00  71.00   0.50   15.82    --  111.75 -61.00-150.00   64
 23  \w     96.00 137.00   0.50   15.82    --  111.75 125.00-120.00   82
 24  \w     45.00  70.00   0.50   15.82    --  111.75 -61.00-180.00   50
 25  \w     97.00 166.00   0.50   15.82    --  111.75  77.00 120.00  138
 26  \w    117.00 158.00   0.50   15.82    --  111.75  30.00 120.00   82
 27  \w     80.00 105.00   0.50   15.82    --  111.75 -77.00 -90.00   50
 28  \w     45.00  70.00   0.50   15.82    --  111.75 -61.00  30.00   50
 29  \w    142.00 168.00   0.50   15.82    --  111.75  45.00 -30.00   52
 30  \w     48.00  78.00   0.50   15.82    --  111.75-125.00-150.00   60
 31  \w     41.00 107.00   0.50   15.82    --  111.75-125.00-120.00  132
;
_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      0.2856562000
_diffrn_orient_matrix_UB_12      -0.0457678000
_diffrn_orient_matrix_UB_13      0.0368812000
_diffrn_orient_matrix_UB_21      0.2287520000
_diffrn_orient_matrix_UB_22      0.0215190000
_diffrn_orient_matrix_UB_23      -0.0736032000
_diffrn_orient_matrix_UB_31      0.1576763000
_diffrn_orient_matrix_UB_32      0.0516262000
_diffrn_orient_matrix_UB_33      0.0633743000
_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  0.0509
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7916
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.529
_diffrn_reflns_theta_min         3.630
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.96a (Rigaku Oxford Diffraction, 2021)
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    1.636
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method 'crystallized from acetone'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.938
_refine_diff_density_min         -1.707
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0615P)^2^+4.2645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2208
_reflns_number_total             2542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01133b2.cif
_cod_data_source_block           2act-Br
_cod_depositor_comments
'Adding full bibliography for 7158173--7158183.cif.'
_cod_original_cell_volume        1226.79(13)
_cod_database_code               7158174
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H8 Br1 N3 O1'
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.566
_reflns_odcompleteness_completeness 99.77
_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), C5(H5), C18(H18), C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              17068
_olex2_date_sample_data_collection 2021-02-19
_olex2_date_sample_submission    2021-02-17
_olex2_exptl_crystal_mounting_method 'mounted on  a MiTegen loop'
_olex2_submission_original_sample_id 2act-Br
_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 2.695
_oxdiff_exptl_absorpt_empirical_full_min 0.548