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_1547269
_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           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 102.2920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8390(2)
_cell_length_b                   11.33640(10)
_cell_length_c                   17.8545(2)
_cell_measurement_reflns_used    15543
_cell_measurement_temperature    123.0
_cell_measurement_theta_max      73.5004
_cell_measurement_theta_min      3.5217
_cell_volume                     2934.64(6)
_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 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega  -98.00   -3.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9564  125.0000  150.0000 95

  2 omega -108.00  -15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9564  -37.0000    0.0000 93

  3 omega   33.00   61.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -77.0000   30.0000 28

  4 omega   73.00  158.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   77.0000  120.0000 85

  5 omega   32.00   77.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000   30.0000 45

  6 omega   32.00   75.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000 -180.0000 43

  7 omega   83.00  135.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -77.0000   30.0000 52

  8 omega   44.00   72.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000 -150.0000 28

  9 omega   26.00   58.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800 -102.0000   48.0000 32

 10 omega   60.00   96.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800 -102.0000   48.0000 36

 11 omega   38.00   77.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000 -120.0000 39

 12 omega -117.00  -15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9564  -37.0000  -90.0000 102

 13 omega -117.00  -15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9564  -37.0000   90.0000 102

 14 omega -120.00   -7.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9564  -77.0000 -120.0000 113

 15 omega   79.00  158.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   45.0000   60.0000 79

 16 omega   79.00  158.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   45.0000 -150.0000 79

 17 omega   26.00  112.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800 -102.0000 -151.0000 86

 18 omega   73.00  148.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   77.0000    0.0000 75

 19 omega   79.00  158.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   45.0000  -90.0000 79

 20 omega   79.00  158.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   45.0000  -30.0000 79
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0298530000
_diffrn_orient_matrix_UB_12      0.0218744000
_diffrn_orient_matrix_UB_13      -0.0763419000
_diffrn_orient_matrix_UB_21      0.0251870000
_diffrn_orient_matrix_UB_22      0.1282219000
_diffrn_orient_matrix_UB_23      0.0244405000
_diffrn_orient_matrix_UB_31      0.0988176000
_diffrn_orient_matrix_UB_32      -0.0392877000
_diffrn_orient_matrix_UB_33      0.0370978000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23347
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         73.662
_diffrn_reflns_theta_min         4.652
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.975
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.773
_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    1.414
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.3072
_exptl_crystal_size_mid          0.1804
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5819
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0555P)^2^+1.8330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5274
_reflns_number_total             5819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            4.cif
_cod_data_source_block           j184
_cod_database_code               1547269
_chemical_oxdiff_formula         'c35 h28 n8 s1'
_reflns_odcompleteness_completeness 99.86
_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. Uiso/Uaniso restraints and constraints
C23 \\sim C22 \\sim C28 \\sim C27 \\sim C26 \\sim C25: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C29(H29A,H29B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31),
  C32(H32), C33(H33), C34(H34), C35(H35), N6(H6A), N8(H8A)
;
_shelx_res_checksum              36017
_shelx_hkl_checksum              28059
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'