The Methyl Group as a Source of Structural Diversity in Heterocyclic Chemistry: Side Chain Functionalization of Picolines and Related Heterocycles
Victor Mamane; Emmanuel Aubert; Yves Fort; Journal of Organic Chemistry 72 (2007) 7294–7300; doi:10.1021/jo071209z

data_4024183
_publ_section_title
;
 The Methyl Group as a Source of Structural Diversity in Heterocyclic
 Chemistry: Side Chain Functionalization of Picolines and
 Related Heterocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7294
_journal_page_last               7300
_journal_paper_doi               10.1021/jo071209z
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C10 H15 N S3'
_chemical_formula_sum            'C10 H15 N S3'
_chemical_formula_weight         245.41
_chemical_name_common            13
_chemical_name_systematic
;
 2-(tris-methylsulfanyl-methyl)-3-methyl-pyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.895(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7373(8)
_cell_length_b                   12.9144(9)
_cell_length_c                   14.3355(9)
_cell_measurement_reflns_used    45831
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.26
_cell_measurement_theta_min      3.31
_cell_volume                     1220.52(18)
_computing_cell_refinement       'HKL Suite (Otwinoski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction
;
'HKL Suite (Otwinoski & Minor, 1997)'
'Sortav (Blessing, R. H. (1997) J. Appl. Cryst. 30, 421-426'
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
'SIR92 Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993)
 J. Appl. Cryst. 26, 343-350.'
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45831
_diffrn_reflns_theta_full        35.00
_diffrn_reflns_theta_max         36.26
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sortav,  Blessing, R. H. (1995) Acta Cryst. A51, 33-38.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0090(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         5679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.1830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                4799
_reflns_number_total             5679
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo071209z-File004.cif
_cod_data_source_block           13
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024183