Tele-substitution Reactions in the Synthesis of a Promising Class of 1,2,4-Triazolo[4,3-a]pyrazine-Based Antimalarials.
Korsik, Marat; Tse, Edwin; Smith, David G.; Lewis, William; Rutledge, Peter J.; Todd, Matthew H.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01045

data_4038891
_publ_section_title
;
 Tele-substitution Reactions in the Synthesis of a Promising Class of
 1,2,4-Triazolo[4,3-a]pyrazine-Based Antimalarials.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01045
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C5 H3 Cl N4'
_chemical_formula_sum            'C5 H3 Cl N4'
_chemical_formula_weight         154.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.963(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9527(2)
_cell_length_b                   6.30259(16)
_cell_length_c                   7.5416(2)
_cell_measurement_reflns_used    3889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6830
_cell_measurement_theta_min      6.4150
_cell_volume                     299.600(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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    -52.00 -16.00   1.00    1.00    --  -40.27  38.00 -60.00   36
  2  \w   -111.00 -16.00   1.00    1.00    --  -40.27 -57.00 150.00   95
  3  \w    -12.00  33.00   1.00    1.00    --  -40.27  38.00 -60.00   45
  4  \w    -38.00  72.00   1.00    1.00    --   40.27 -77.00  60.00  110
  5  \w      9.00  60.00   1.00    1.00    --   40.27  77.00   0.00   51
  6  \w      9.00  35.00   1.00    1.00    --   40.27  77.00 -60.00   26
  7  \w    135.00 178.00   1.00    3.00    --  113.00  77.00 150.00   43
  8  \w    148.00 173.00   1.00    3.00    --  113.00  45.00   0.00   25
  9  \w     88.00 141.00   1.00    3.00    --  113.00  45.00 -60.00   53
 10  \w    105.00 131.00   1.00    3.00    --  113.00  45.00   0.00   26
 11  \w     69.00  96.00   1.00    3.00    --  113.00 -77.00   0.00   27
 12  \w    104.00 130.00   1.00    3.00    --  113.00  45.00-150.00   26
 13  \w     46.00 111.00   1.00    3.00    --  113.00 -77.00-180.00   65
 14  \w    106.00 178.00   1.00    3.00    --  113.00  45.00 -30.00   72
 15  \w     85.00 135.00   1.00    3.00    --  113.00  77.00 120.00   50
 16  \w     44.00 147.00   1.00    3.00    --  113.00 -77.00 -60.00  103
 17  \w     74.00 145.00   1.00    3.00    --  113.00 -80.00  46.74   71
 18  \w     80.00 106.00   1.00    3.00    --  113.00 -77.00-120.00   26
 19  \w     36.00  61.00   1.00    3.00    --  113.00 -80.00  46.74   25
 20  \w    144.00 177.00   1.00    3.00    --  113.00  45.00-150.00   33
 21  \w     47.00 142.00   1.00    3.00    --  113.00 -61.00-150.00   95
 22  \w     41.00  66.00   1.00    3.00    --  113.00 -77.00   0.00   25
 23  \w     96.00 176.00   1.00    3.00    --  113.00  77.00-120.00   80
 24  \w     94.00 119.00   1.00    3.00    --  113.00  45.00  90.00   25
 25  \w     86.00 133.00   1.00    3.00    --  113.00  77.00-150.00   47
 26  \w     68.00 119.00   1.00    3.00    --  113.00 -80.00  86.56   51
 27  \w    -37.00  73.00   1.00    1.00    --   40.00 -73.80   0.00  110
 28  \w    -37.00  73.00   1.00    1.00    --   40.00 -73.80  90.00  110
 29  \w    -37.00  73.00   1.00    1.00    --   40.00 -73.80 180.00  110
 30  \w    -37.00  73.00   1.00    1.00    --   40.00 -73.80 270.00  110
 31  \w     33.00 143.00   1.00    3.00    --  110.00 -73.80   0.00  110
 32  \w     33.00 143.00   1.00    3.00    --  110.00 -73.80  90.00  110
 33  \w     33.00 143.00   1.00    3.00    --  110.00 -73.80 180.00  110
 34  \w     33.00 143.00   1.00    3.00    --  110.00 -73.80 270.00  110
 35  \w      7.00 117.00   1.00    1.00    --   40.00  73.80   0.00  110
 36  \w      7.00 117.00   1.00    1.00    --   40.00  73.80  90.00  110
 37  \w      7.00 117.00   1.00    1.00    --   40.00  73.80 180.00  110
 38  \w      7.00 117.00   1.00    1.00    --   40.00  73.80 270.00  110
 39  \w     77.00 178.00   1.00    3.00    --  110.00  73.80   0.00  101
 40  \w     77.00 178.00   1.00    3.00    --  110.00  73.80  90.00  101
 41  \w     77.00 178.00   1.00    3.00    --  110.00  73.80 180.00  101
 42  \w     77.00 178.00   1.00    3.00    --  110.00  73.80 270.00  101
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1183552000
_diffrn_orient_matrix_UB_12      -0.2092369000
_diffrn_orient_matrix_UB_13      0.0828449000
_diffrn_orient_matrix_UB_21      0.1999585000
_diffrn_orient_matrix_UB_22      0.0902199000
_diffrn_orient_matrix_UB_23      -0.0124771000
_diffrn_orient_matrix_UB_31      0.0761765000
_diffrn_orient_matrix_UB_32      0.0882888000
_diffrn_orient_matrix_UB_33      0.2091025000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5100
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.996
_diffrn_reflns_theta_min         6.474
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    4.929
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.385
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_description       block
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0443P)^2^+0.2900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                686
_reflns_number_total             686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            mht18pt5_s1649.cif
_cod_data_source_block           mht18pt5_s1649
_cod_database_code               4038891
_sydney_internal_submission_code mht18pt5_s1649
_sydney_internal_submission_date 2015-07-30
_sydney_internal_submission_number s1649
_sydney_internal_client_code     mkr
_sydney_internal_client_email    mkor7275@uni.sydney.edu.au
_sydney_internal_client_name     'Marat Korsik'
_sydney_internal_supervisor_code mht
_sydney_internal_supervisor_name 'Matt Todd'
_sydney_internal_collection_date 2018-08-01
_sydney_internal_collection_user petert
_sydney_internal_process_date    2019-05-23
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-05-23
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-05-23
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-05-23
_sydney_internal_check_user      wlew0588
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C5H3ClN4
_shelx_estimated_absorpt_t_max   0.740
_shelx_estimated_absorpt_t_min   0.373
_reflns_odcompleteness_completeness 98.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C8(H8)
;
_shelx_res_checksum              5234
_shelx_hkl_checksum              7750
_olex2_date_sample_data_collection 2018-08-01
_olex2_date_sample_submission    2018-07-30
_olex2_exptl_crystal_mounting_method 'in paratone on a loop'
_olex2_submission_original_sample_id MK002-8
_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.788