Iodine-Catalyzed Chemoselective Hydroamination Reaction Using 5-Mercaptotetrazoles Derivatives.
Siddaraju, Yogesh; Prabhu, Kandikere Ramaiah; ACS omega 3 (2018) 4908–4917; doi:10.1021/acsomega.8b00499

data_4515998
_publ_section_title
;
 Iodine-Catalyzed Chemoselective Hydroamination Reaction Using
 5-Mercaptotetrazoles Derivatives.
;
_journal_issue                   5
_journal_name_full               'ACS omega'
_journal_page_first              4908
_journal_page_last               4917
_journal_paper_doi               10.1021/acsomega.8b00499
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C13 H18 N4 S'
_chemical_formula_sum            'C13 H18 N4 S'
_chemical_formula_weight         262.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                82.547(13)
_cell_angle_beta                 79.592(13)
_cell_angle_gamma                67.366(12)
_cell_formula_units_Z            2
_cell_length_a                   7.720(4)
_cell_length_b                   8.727(5)
_cell_length_c                   11.731(6)
_cell_measurement_reflns_used    6365
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.884
_cell_measurement_theta_min      1.769
_cell_volume                     715.9(7)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.1927
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16712
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.769
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.0424
_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/[\s^2^(Fo^2^)+(0.0695P)^2^+0.0228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1671
_reflns_number_total             2518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b00499_si_002.cif
_cod_data_source_block           red
_cod_original_cell_volume        715.8(7)
_cod_database_code               4515998
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Me refined with riding coordinates:
 C32(H32A,H32B,H32C)
2.c Aromatic/amide H refined with riding coordinates:
 C011(H011), C012(H012)
2.d Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C), C015(H01D,H01E,H01F), C016(H01G,H01H,H01I), C017(H01J,
 H01K,H01L)
;
_olex2_submission_special_instructions 'No special instructions were received'