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_1547271
_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 H19 Br N4 S'
_chemical_formula_sum            'C20 H19 Br N4 S'
_chemical_formula_weight         427.36
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 93.8246(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.13384(13)
_cell_length_b                   21.7680(3)
_cell_length_c                   9.47711(13)
_cell_measurement_reflns_used    4770
_cell_measurement_temperature    123
_cell_measurement_theta_max      71.2969
_cell_measurement_theta_min      4.0583
_cell_volume                     1880.09(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_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      123.15
_diffrn_detector_area_resol_mean 10.3546
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega   20.00   59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8939   37.0000 -180.0000 39

  2 omega  -35.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8939  -37.0000  -60.0000 98

  3 omega    4.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8939 -125.0000  -90.0000 64

  4 omega   73.00  131.00   1.0000    3.4100
omega____ theta____ kappa____ phi______ frames
    -      102.3929  125.0000  -30.0000 58

  5 omega   55.00  136.00   1.0000    3.4100
omega____ theta____ kappa____ phi______ frames
    -      102.3929  -77.0000 -180.0000 81

  6 omega   80.00  109.00   1.0000    3.4100
omega____ theta____ kappa____ phi______ frames
    -      102.3929   45.0000  -30.0000 29

  7 omega   28.00   68.00   1.0000    3.4100
omega____ theta____ kappa____ phi______ frames
    -      102.3929  -45.0000  -30.0000 40

  8 omega   30.00   57.00   1.0000    3.4100
omega____ theta____ kappa____ phi______ frames
    -      102.3929  -45.0000 -180.0000 27

  9 omega   76.00  158.00   1.0000    3.4100
omega____ theta____ kappa____ phi______ frames
    -      102.3929   77.0000  120.0000 82

 10 omega   94.00  157.00   1.0000    3.4100
omega____ theta____ kappa____ phi______ frames
    -      102.3929  125.0000  -60.0000 63

 11 omega   75.00  125.00   1.0000    3.4100
omega____ theta____ kappa____ phi______ frames
    -      102.3929   77.0000 -120.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1111046000
_diffrn_orient_matrix_UB_12      -0.0531644000
_diffrn_orient_matrix_UB_13      0.0160382000
_diffrn_orient_matrix_UB_21      -0.1131146000
_diffrn_orient_matrix_UB_22      -0.0387683000
_diffrn_orient_matrix_UB_23      0.0742593000
_diffrn_orient_matrix_UB_31      -0.0587632000
_diffrn_orient_matrix_UB_32      -0.0260303000
_diffrn_orient_matrix_UB_33      -0.1441024000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6987
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.438
_diffrn_reflns_theta_min         4.062
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.100
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_correction_T_min  0.394
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
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            'translucent colourless'
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.5217
_exptl_crystal_size_mid          0.1035
_exptl_crystal_size_min          0.0384
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0494P)^2^+0.2465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3024
_reflns_number_total             3533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            8.cif
_cod_data_source_block           j181
_cod_database_code               1547271
_chemical_oxdiff_formula         'c20 h19 n4 s1 br1'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_shelx_res_checksum              12507
_shelx_hkl_checksum              40762
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'