#------------------------------------------------------------------------------
#$Date: 2020-10-15 02:19:17 +0300 (Thu, 15 Oct 2020) $
#$Revision: 258401 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038891.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038891
loop_
_publ_author_name
'Korsik, Marat'
'Tse, Edwin'
'Smith, David G.'
'Lewis, William'
'Rutledge, Peter J.'
'Todd, Matthew H.'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -52.00 -16.00   1.00    1.00    --  -40.27  38.00 -60.00   36
  2  ω   -111.00 -16.00   1.00    1.00    --  -40.27 -57.00 150.00   95
  3  ω    -12.00  33.00   1.00    1.00    --  -40.27  38.00 -60.00   45
  4  ω    -38.00  72.00   1.00    1.00    --   40.27 -77.00  60.00  110
  5  ω      9.00  60.00   1.00    1.00    --   40.27  77.00   0.00   51
  6  ω      9.00  35.00   1.00    1.00    --   40.27  77.00 -60.00   26
  7  ω    135.00 178.00   1.00    3.00    --  113.00  77.00 150.00   43
  8  ω    148.00 173.00   1.00    3.00    --  113.00  45.00   0.00   25
  9  ω     88.00 141.00   1.00    3.00    --  113.00  45.00 -60.00   53
 10  ω    105.00 131.00   1.00    3.00    --  113.00  45.00   0.00   26
 11  ω     69.00  96.00   1.00    3.00    --  113.00 -77.00   0.00   27
 12  ω    104.00 130.00   1.00    3.00    --  113.00  45.00-150.00   26
 13  ω     46.00 111.00   1.00    3.00    --  113.00 -77.00-180.00   65
 14  ω    106.00 178.00   1.00    3.00    --  113.00  45.00 -30.00   72
 15  ω     85.00 135.00   1.00    3.00    --  113.00  77.00 120.00   50
 16  ω     44.00 147.00   1.00    3.00    --  113.00 -77.00 -60.00  103
 17  ω     74.00 145.00   1.00    3.00    --  113.00 -80.00  46.74   71
 18  ω     80.00 106.00   1.00    3.00    --  113.00 -77.00-120.00   26
 19  ω     36.00  61.00   1.00    3.00    --  113.00 -80.00  46.74   25
 20  ω    144.00 177.00   1.00    3.00    --  113.00  45.00-150.00   33
 21  ω     47.00 142.00   1.00    3.00    --  113.00 -61.00-150.00   95
 22  ω     41.00  66.00   1.00    3.00    --  113.00 -77.00   0.00   25
 23  ω     96.00 176.00   1.00    3.00    --  113.00  77.00-120.00   80
 24  ω     94.00 119.00   1.00    3.00    --  113.00  45.00  90.00   25
 25  ω     86.00 133.00   1.00    3.00    --  113.00  77.00-150.00   47
 26  ω     68.00 119.00   1.00    3.00    --  113.00 -80.00  86.56   51
 27  ω    -37.00  73.00   1.00    1.00    --   40.00 -73.80   0.00  110
 28  ω    -37.00  73.00   1.00    1.00    --   40.00 -73.80  90.00  110
 29  ω    -37.00  73.00   1.00    1.00    --   40.00 -73.80 180.00  110
 30  ω    -37.00  73.00   1.00    1.00    --   40.00 -73.80 270.00  110
 31  ω     33.00 143.00   1.00    3.00    --  110.00 -73.80   0.00  110
 32  ω     33.00 143.00   1.00    3.00    --  110.00 -73.80  90.00  110
 33  ω     33.00 143.00   1.00    3.00    --  110.00 -73.80 180.00  110
 34  ω     33.00 143.00   1.00    3.00    --  110.00 -73.80 270.00  110
 35  ω      7.00 117.00   1.00    1.00    --   40.00  73.80   0.00  110
 36  ω      7.00 117.00   1.00    1.00    --   40.00  73.80  90.00  110
 37  ω      7.00 117.00   1.00    1.00    --   40.00  73.80 180.00  110
 38  ω      7.00 117.00   1.00    1.00    --   40.00  73.80 270.00  110
 39  ω     77.00 178.00   1.00    3.00    --  110.00  73.80   0.00  101
 40  ω     77.00 178.00   1.00    3.00    --  110.00  73.80  90.00  101
 41  ω     77.00 178.00   1.00    3.00    --  110.00  73.80 180.00  101
 42  ω     77.00 178.00   1.00    3.00    --  110.00  73.80 270.00  101
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω 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/[σ²(Fo²)+(0.0443P)²+0.2900P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9279(3) 0.250000 0.2545(3) 0.0114(4) Uani 1 2 d S T P . .
C2 C 1.1440(3) 0.250000 0.3405(3) 0.0141(5) Uani 1 2 d S T P . .
H2 H 1.232088 0.250000 0.272577 0.017 Uiso 1 2 calc RS T P . .
N3 N 1.2120(3) 0.250000 0.5312(3) 0.0161(4) Uani 1 2 d S T P . .
N4 N 1.0388(3) 0.250000 0.5767(3) 0.0152(4) Uani 1 2 d S T P . .
C5 C 0.8685(4) 0.250000 0.4081(3) 0.0127(5) Uani 1 2 d S T P . .
C6 C 0.6478(4) 0.250000 0.3606(3) 0.0157(5) Uani 1 2 d S T P . .
H6 H 0.603275 0.250000 0.463602 0.019 Uiso 1 2 calc RS T P . .
N7 N 0.5041(3) 0.250000 0.1797(3) 0.0164(4) Uani 1 2 d S T P . .
C8 C 0.5689(4) 0.250000 0.0302(3) 0.0150(5) Uani 1 2 d S T P . .
H8 H 0.464098 0.250000 -0.101089 0.018 Uiso 1 2 calc RS T P . .
C9 C 0.7765(4) 0.250000 0.0635(3) 0.0131(5) Uani 1 2 d S T P . .
Cl10 Cl 0.86934(8) 0.250000 -0.11319(7) 0.0158(2) Uani 1 2 d S T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0359
0 -1 0 0.0359
1 0 -1 0.0274
-1 0 1 0.0374
2 1 3 0.1124
0 0 -1 0.0948
-4 -1 2 0.0672
-3 -3 2 0.0377
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 105.09(18) . . ?
C2 N1 C9 134.4(2) . . ?
C9 N1 C5 120.51(19) . . ?
N1 C2 H2 125.2 . . ?
N3 C2 N1 109.70(19) . . ?
N3 C2 H2 125.2 . . ?
C2 N3 N4 108.88(19) . . ?
C5 N4 N3 106.33(18) . . ?
N1 C5 C6 117.4(2) . . ?
N4 C5 N1 110.01(19) . . ?
N4 C5 C6 132.5(2) . . ?
C5 C6 H6 118.9 . . ?
N7 C6 C5 122.1(2) . . ?
N7 C6 H6 118.9 . . ?
C6 N7 C8 118.9(2) . . ?
N7 C8 H8 118.7 . . ?
C9 C8 N7 122.5(2) . . ?
C9 C8 H8 118.7 . . ?
N1 C9 Cl10 116.18(17) . . ?
C8 C9 N1 118.5(2) . . ?
C8 C9 Cl10 125.35(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.362(3) . ?
N1 C5 1.385(3) . ?
N1 C9 1.380(3) . ?
C2 H2 0.9500 . ?
C2 N3 1.311(3) . ?
N3 N4 1.385(3) . ?
N4 C5 1.322(3) . ?
C5 C6 1.420(3) . ?
C6 H6 0.9500 . ?
C6 N7 1.307(3) . ?
N7 C8 1.379(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.357(3) . ?
C9 Cl10 1.708(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 N3 N4 0.000(1) . . . . ?
N1 C5 C6 N7 0.000(1) . . . . ?
C2 N1 C5 N4 0.000(1) . . . . ?
C2 N1 C5 C6 180.000(0) . . . . ?
C2 N1 C9 C8 180.000(0) . . . . ?
C2 N1 C9 Cl10 0.000(0) . . . . ?
C2 N3 N4 C5 0.000(1) . . . . ?
N3 N4 C5 N1 0.000(1) . . . . ?
N3 N4 C5 C6 180.000(1) . . . . ?
N4 C5 C6 N7 180.000(1) . . . . ?
C5 N1 C2 N3 0.000(1) . . . . ?
C5 N1 C9 C8 0.000(0) . . . . ?
C5 N1 C9 Cl10 180.000(0) . . . . ?
C5 C6 N7 C8 0.000(1) . . . . ?
C6 N7 C8 C9 0.000(0) . . . . ?
N7 C8 C9 N1 0.000(0) . . . . ?
N7 C8 C9 Cl10 180.000(0) . . . . ?
C9 N1 C2 N3 180.000(1) . . . . ?
C9 N1 C5 N4 180.000(1) . . . . ?
C9 N1 C5 C6 0.000(1) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.9994 -0.0002 -0.2091 0.0902 0.0882
0.0000 -0.9994 0.0002 0.2091 -0.0902 -0.0882
0.9991 0.0006 -0.9994 0.0353 0.2123 -0.1328
-0.9991 -0.0006 0.9994 -0.0353 -0.2123 0.1328
2.0011 1.0003 2.9938 0.2756 0.4530 0.8668
-0.0006 0.0001 -0.9986 -0.0828 0.0123 -0.2088
-3.9974 -1.0016 2.0007 -0.0978 -0.9146 0.0254
-2.9977 -2.9999 2.0001 0.4386 -0.8950 -0.0750
