Halo-1,2,3-triazolium Salts as Halogen Bond Donors for the Activation of Imines in Dihydropyridinone Synthesis.
Kaasik, Mikk; Metsala, Andrus; Kaabel, Sandra; Kriis, Kadri; Järving, Ivar; Kanger, Tõnis; The Journal of organic chemistry 84 (2019) 4294–4303; doi:10.1021/acs.joc.9b00248

data_4034249
_publ_section_title
;
 Halo-1,2,3-triazolium Salts as Halogen Bond Donors for the Activation of
 Imines in Dihydropyridinone Synthesis.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4294
_journal_page_last               4303
_journal_paper_doi               10.1021/acs.joc.9b00248
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 I N4 O2, B F4'
_chemical_formula_sum            'C17 H16 B F4 I N4 O2'
_chemical_formula_weight         522.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.965(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.54000(10)
_cell_length_b                   19.8361(4)
_cell_length_c                   15.2529(3)
_cell_measurement_reflns_used    11699
_cell_measurement_temperature    123.0
_cell_measurement_theta_max      67.1030
_cell_measurement_theta_min      2.8960
_cell_volume                     1973.99(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection
;
Rigaku CollectionStrategy through HKL-3000 program package
Minor, W., Cymborowski, M., Otwinowski, Z., Chruszcz, M. (2011) 
Acta Cryst. D62, 859-866
;
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
Mercury CSD 3.10.1 (Macrae, C. F., et al. (2006). J. Appl. Cryst. 39, 453-457)
POV-Ray 3.7 (Persistence of Vision Pty. Ltd. (2004)) 
;
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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   -179.00  -0.50   1.50   15.00    --  -90.00  60.00  36.00  119
  2  \w   -110.00  68.50   1.50   15.00    --  -21.00  60.00 -36.00  119
  3  \w   -179.00  -0.50   1.50   15.00    --  -90.00  30.00 -36.00  119
  4  \w   -179.00  -0.50   1.50   15.00    --  -90.00  60.00-108.00  119
  5  \w   -179.00  -0.50   1.50   15.00    --  -90.00   0.00  36.00  119
  6  \w   -179.00  -0.50   1.50   15.00    --  -90.00  60.00-180.00  119
  7  \w   -179.00  -0.50   1.50   15.00    --  -90.00  30.00  36.00  119
  8  \w   -179.00  -0.50   1.50   15.00    --  -90.00  30.00-108.00  119
  9  \w   -179.00  -0.50   1.50   15.00    --  -90.00  60.00 -36.00  119
 10  \w   -110.00  68.50   1.50   15.00    --  -21.00  30.00  36.00  119
 11  \w   -179.00 -99.50   1.50   15.00    --  -90.00  30.00 108.00   53
;
_diffrn_measurement_device       'Rigaku Compact HomeLab'
_diffrn_measurement_device_type  'Rigaku Saturn944+ (2x2 bin mode)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1882924000
_diffrn_orient_matrix_UB_12      -0.0336346000
_diffrn_orient_matrix_UB_13      -0.0480008000
_diffrn_orient_matrix_UB_21      0.0266093000
_diffrn_orient_matrix_UB_22      0.0447634000
_diffrn_orient_matrix_UB_23      -0.0809909000
_diffrn_orient_matrix_UB_31      0.1397655000
_diffrn_orient_matrix_UB_32      -0.0538547000
_diffrn_orient_matrix_UB_33      -0.0373139000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26048
_diffrn_reflns_point_group_measured_fraction_full 0.860
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        67.383
_diffrn_reflns_theta_max         67.383
_diffrn_reflns_theta_min         2.904
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-003'
_exptl_absorpt_coefficient_mu    13.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.757
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.218
_refine_diff_density_min         -1.678
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.034(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         6111
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0923P)^2^+1.3470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.717
_reflns_Friedel_fraction_max     0.717
_reflns_number_gt                5765
_reflns_number_total             6111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00248_si_004.cif
_cod_data_source_block           8c
_cod_depositor_comments
;

2020-05-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C17 H16 I N4 O2), 2(B F4)'
_cod_original_formula_sum        'C34 H32 B2 F8 I2 N8 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1044.09
_cod_database_code               4034249
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C18 H16 N4 O5 F3 S1 I1'
_shelx_estimated_absorpt_t_max   0.691
_shelx_estimated_absorpt_t_min   0.277
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.27
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9B(H9B), C9A(H9A)
2.b Aromatic/amide H refined with riding coordinates:
 C14A(H14A), C16B(H16B), C8A(H8A), C8B(H8B), C17A(H17A), C7B(H7B), C15B(H15B),
 C7A(H7A), C13B(H13B), C15A(H15A), C17B(H17B), C16A(H16A), C4B(H4B), C13A(H13A),
  C14B(H14B), C5B(H5B), C5A(H5A), C4A(H4A)
2.c Idealised Me refined as rotating group:
 C11B(H11D,H11E,H11F), C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F), C11A(H11A,
 H11B,H11C)
;
_shelx_res_checksum              16325
_shelx_hkl_checksum              77137
_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 2.886
_oxdiff_exptl_absorpt_empirical_full_min 0.365