#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/41/4024183.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024183
loop_
_publ_author_name
'Victor Mamane'
'Emmanuel Aubert'
'Yves Fort'
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0368P)²+0.1830P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.84670(3) 0.368512(15) 0.455099(13) 0.01877(5) Uani 1 1 d . . .
S1 S 0.43065(3) 0.269763(18) 0.436877(14) 0.02316(5) Uani 1 1 d . . .
S3 S 0.77116(3) 0.166336(17) 0.549338(13) 0.02336(5) Uani 1 1 d . . .
N1 N 0.86072(11) 0.24577(6) 0.30678(5) 0.02107(12) Uani 1 1 d . . .
C2 C 0.74033(11) 0.19214(6) 0.35311(5) 0.01700(12) Uani 1 1 d . . .
C3 C 0.65802(12) 0.09451(6) 0.32094(5) 0.02029(13) Uani 1 1 d . . .
C4 C 0.71262(13) 0.05500(7) 0.23927(6) 0.02411(15) Uani 1 1 d . . .
H4 H 0.6650 -0.0114 0.2165 0.029 Uiso 1 1 calc R . .
C11 C 0.51648(16) 0.03051(8) 0.36609(7) 0.03140(19) Uani 1 1 d . . .
H11B H 0.4826 -0.0336 0.3297 0.047 Uiso 1 1 calc R . .
H11A H 0.3921 0.0699 0.3662 0.047 Uiso 1 1 calc R . .
H11C H 0.5825 0.0136 0.4318 0.047 Uiso 1 1 calc R . .
C6 C 0.90546(13) 0.20629(7) 0.22695(6) 0.02562(16) Uani 1 1 d . . .
H6 H 0.9887 0.2455 0.1940 0.031 Uiso 1 1 calc R . .
C9 C 0.77399(15) 0.42175(7) 0.55915(6) 0.02860(17) Uani 1 1 d . . .
H9A H 0.6267 0.4320 0.5463 0.043 Uiso 1 1 calc R . .
H9B H 0.8422 0.4884 0.5750 0.043 Uiso 1 1 calc R . .
H9C H 0.8135 0.3739 0.6128 0.043 Uiso 1 1 calc R . .
C7 C 0.70154(11) 0.24684(6) 0.44237(5) 0.01681(12) Uani 1 1 d . . .
C10 C 1.03630(16) 0.14469(9) 0.55264(8) 0.0352(2) Uani 1 1 d . . .
H10B H 1.0519 0.1061 0.4957 0.053 Uiso 1 1 calc R . .
H10C H 1.0953 0.1047 0.6097 0.053 Uiso 1 1 calc R . .
H10A H 1.1062 0.2114 0.5543 0.053 Uiso 1 1 calc R . .
C8 C 0.36326(14) 0.33929(8) 0.32618(7) 0.02959(17) Uani 1 1 d . . .
H8A H 0.4509 0.4002 0.3282 0.044 Uiso 1 1 calc R . .
H8C H 0.2214 0.3615 0.3164 0.044 Uiso 1 1 calc R . .
H8B H 0.3808 0.2941 0.2736 0.044 Uiso 1 1 calc R . .
C5 C 0.83511(14) 0.11083(8) 0.19072(6) 0.02653(16) Uani 1 1 d . . .
H5 H 0.8696 0.0843 0.1343 0.032 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S2 C7 100.28(4) . . ?
C8 S1 C7 100.75(4) . . ?
C10 S3 C7 101.06(4) . . ?
C2 N1 C6 119.38(7) . . ?
N1 C2 C3 122.31(6) . . ?
N1 C2 C7 113.60(6) . . ?
C3 C2 C7 124.08(6) . . ?
C4 C3 C2 116.49(7) . . ?
C4 C3 C11 117.41(7) . . ?
C2 C3 C11 126.10(7) . . ?
C5 C4 C3 121.24(8) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
N1 C6 C5 122.60(7) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
S2 C9 H9A 109.5 . . ?
S2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C7 S3 112.31(5) . . ?
C2 C7 S1 112.23(5) . . ?
S3 C7 S1 102.03(3) . . ?
C2 C7 S2 107.35(4) . . ?
S3 C7 S2 111.26(4) . . ?
S1 C7 S2 111.73(4) . . ?
S3 C10 H10B 109.5 . . ?
S3 C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S3 C10 H10A 109.5 . . ?
H10B C10 H10A 109.5 . . ?
H10C C10 H10A 109.5 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
C6 C5 C4 117.93(7) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C9 1.7997(8) . ?
S2 C7 1.8400(7) . ?
S1 C8 1.7982(10) . ?
S1 C7 1.8345(8) . ?
S3 C10 1.7990(11) . ?
S3 C7 1.8318(7) . ?
N1 C2 1.3419(9) . ?
N1 C6 1.3427(10) . ?
C2 C3 1.4158(11) . ?
C2 C7 1.5306(10) . ?
C3 C4 1.3942(11) . ?
C3 C11 1.5053(11) . ?
C4 C5 1.3864(12) . ?
C4 H4 0.9500 . ?
C11 H11B 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11C 0.9800 . ?
C6 C5 1.3831(13) . ?
C6 H6 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10A 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8B 0.9800 . ?
C5 H5 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.11(12) . . . . ?
C6 N1 C2 C7 -179.65(7) . . . . ?
N1 C2 C3 C4 1.59(12) . . . . ?
C7 C2 C3 C4 -178.68(7) . . . . ?
N1 C2 C3 C11 -177.81(9) . . . . ?
C7 C2 C3 C11 1.93(13) . . . . ?
C2 C3 C4 C5 -2.31(13) . . . . ?
C11 C3 C4 C5 177.14(9) . . . . ?
C2 N1 C6 C5 -1.17(13) . . . . ?
N1 C2 C7 S3 -124.37(6) . . . . ?
C3 C2 C7 S3 55.87(9) . . . . ?
N1 C2 C7 S1 121.36(6) . . . . ?
C3 C2 C7 S1 -58.40(9) . . . . ?
N1 C2 C7 S2 -1.78(8) . . . . ?
C3 C2 C7 S2 178.46(6) . . . . ?
C10 S3 C7 C2 59.40(6) . . . . ?
C10 S3 C7 S1 179.77(5) . . . . ?
C10 S3 C7 S2 -60.96(6) . . . . ?
C8 S1 C7 C2 -54.94(6) . . . . ?
C8 S1 C7 S3 -175.36(4) . . . . ?
C8 S1 C7 S2 65.70(5) . . . . ?
C9 S2 C7 C2 177.97(6) . . . . ?
C9 S2 C7 S3 -58.79(5) . . . . ?
C9 S2 C7 S1 54.52(5) . . . . ?
N1 C6 C5 C4 0.44(14) . . . . ?
C3 C4 C5 C6 1.37(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658847
