Regioselectivity of the alkylation of S-substituted 1,2,4-triazoles with dihaloalkanes
Ahmed T. A. Boraei; El Sayed H. El Ashry; Axel Duerkop; Chemistry Central Journal 10 (2016) 22–; doi:10.1186/s13065-016-0165-0

data_1547268
_publ_section_title
;
 Regioselectivity of the alkylation of S-substituted 1,2,4-triazoles with
 dihaloalkanes
;
_journal_name_full               'Chemistry Central Journal'
_journal_page_first              22
_journal_paper_doi               10.1186/s13065-016-0165-0
_journal_volume                  10
_journal_year                    2016
_chemical_formula_moiety         'C20 H18 N4 S'
_chemical_formula_sum            'C20 H18 N4 S'
_chemical_formula_weight         346.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                68.513(5)
_cell_angle_beta                 80.348(4)
_cell_angle_gamma                64.771(5)
_cell_formula_units_Z            2
_cell_length_a                   9.0486(4)
_cell_length_b                   9.1081(5)
_cell_length_c                   11.7993(6)
_cell_measurement_reflns_used    4264
_cell_measurement_temperature    123.0
_cell_measurement_theta_max      72.9627
_cell_measurement_theta_min      4.0235
_cell_volume                     818.47(8)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_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    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      123.0
_diffrn_detector_area_resol_mean 10.3546
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
  1 omega  -34.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8939  -37.0000   30.0000 101

  2 omega   65.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8939 -125.0000    0.0000 26

  3 omega   23.00   54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8939 -125.0000    0.0000 31

  4 omega    5.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8939 -125.0000  -30.0000 90

  5 omega   16.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8939   37.0000 -150.0000 92

  6 omega   38.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267  -45.0000   90.0000 26

  7 omega   33.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267  -45.0000 -120.0000 42

  8 omega   31.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267  -45.0000 -150.0000 45

  9 omega   27.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267  -77.0000   90.0000 105

 10 omega   69.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267 -115.0000  -54.0000 48

 11 omega   79.00  157.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267   45.0000   30.0000 78

 12 omega   98.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267  -77.0000 -120.0000 38

 13 omega   89.00  142.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267   45.0000 -180.0000 53

 14 omega   43.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267  -45.0000  -90.0000 33

 15 omega   34.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267  -15.0000    0.0000 122

 16 omega   34.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267 -123.0000  -93.0000 71

 17 omega   33.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      106.0267 -106.0000   70.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0034633000
_diffrn_orient_matrix_UB_12      0.1065112000
_diffrn_orient_matrix_UB_13      0.0768499000
_diffrn_orient_matrix_UB_21      -0.1734855000
_diffrn_orient_matrix_UB_22      0.1283236000
_diffrn_orient_matrix_UB_23      -0.0450346000
_diffrn_orient_matrix_UB_31      -0.0729320000
_diffrn_orient_matrix_UB_32      -0.1069553000
_diffrn_orient_matrix_UB_33      0.1084365000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5423
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.118
_diffrn_reflns_theta_min         4.027
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.826
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Stick
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.5142
_exptl_crystal_size_mid          0.1369
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.3043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2966
_reflns_number_total             3154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            10.cif
_cod_data_source_block           j186
_cod_database_code               1547268
_chemical_oxdiff_formula         'C20 H18 N4 S1'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_shelx_res_checksum              89282
_shelx_hkl_checksum              35182
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'