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_1547270
_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         'C35 H28 N8 S2'
_chemical_formula_sum            'C35 H28 N8 S2'
_chemical_formula_weight         624.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 106.0192(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.9005(5)
_cell_length_b                   8.04840(12)
_cell_length_c                   11.51861(19)
_cell_measurement_reflns_used    8294
_cell_measurement_temperature    123.0
_cell_measurement_theta_max      73.4248
_cell_measurement_theta_min      3.9895
_cell_volume                     2931.65(8)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_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 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -98.00  -15.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8939  -37.0000    0.0000 83

  2 omega  -23.00   30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8939   37.0000  120.0000 53

  3 omega  -54.00   -3.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8939  125.0000  120.0000 51

  4 omega -108.00  -39.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8939  -37.0000  -60.0000 69

  5 omega    3.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939 -125.0000  -60.0000 72

  6 omega   58.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939 -137.0000  120.0000 47

  7 omega   28.00  141.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -77.0000   90.0000 113

  8 omega   45.00   70.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000 -180.0000 25

  9 omega   41.00   76.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000  -90.0000 35

 10 omega   45.00  123.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -77.0000  -30.0000 78

 11 omega   82.00  139.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -77.0000 -180.0000 57

 12 omega   93.00  154.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -15.0000   30.0000 61

 13 omega   79.00  105.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   45.0000 -120.0000 26

 14 omega   33.00   58.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000  -60.0000 25

 15 omega   83.00  153.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   45.0000   60.0000 70

 16 omega   92.00  152.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   45.0000  -60.0000 60

 17 omega   85.00  112.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800 -122.0000 -131.0000 27

 18 omega   28.00   54.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -77.0000 -180.0000 26

 19 omega   79.00  157.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   45.0000   30.0000 78

 20 omega   36.00   74.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000   90.0000 38

 21 omega   27.00   77.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -15.0000   30.0000 50

 22 omega   97.00  125.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800 -132.0000  117.0000 28

 23 omega   87.00  112.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800 -110.0000  -67.0000 25

 24 omega   29.00   63.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800 -110.0000  -67.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0430039000
_diffrn_orient_matrix_UB_12      -0.0112890000
_diffrn_orient_matrix_UB_13      -0.0284536000
_diffrn_orient_matrix_UB_21      0.0228561000
_diffrn_orient_matrix_UB_22      0.0132980000
_diffrn_orient_matrix_UB_23      0.1357018000
_diffrn_orient_matrix_UB_31      -0.0009346000
_diffrn_orient_matrix_UB_32      -0.1907006000
_diffrn_orient_matrix_UB_33      0.0110845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10434
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         26.241
_diffrn_reflns_theta_min         2.576
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
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    1.416
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.3518
_exptl_crystal_size_mid          0.0477
_exptl_crystal_size_min          0.0413
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+2.4513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2824
_reflns_number_total             2927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            6.cif
_cod_data_source_block           j185
_cod_database_code               1547270
_chemical_oxdiff_formula         'c35 h28 n8 s2'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_shelx_res_checksum              80341
_shelx_hkl_checksum              62152
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'