#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/41/4024184.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_4024184
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         'C24 H19 N S3'
_chemical_formula_sum            'C24 H19 N S3'
_chemical_formula_weight         417.58
_chemical_name_common            25
_chemical_name_systematic
;
 2-(tris-phenylsulfanyl-methyl)-pyridine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.479(4)
_cell_angle_beta                 106.581(4)
_cell_angle_gamma                111.661(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2196(4)
_cell_length_b                   10.2735(7)
_cell_length_c                   13.8570(11)
_cell_measurement_reflns_used    59580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.02
_cell_measurement_theta_min      3.45
_cell_volume                     1027.68(12)
_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 0.993
_diffrn_measured_fraction_theta_max 0.915
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            59580
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.02
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.864
_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    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         6553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0291
_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)+(0.0371P)²+0.4469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                6016
_reflns_number_total             6553
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo071209z-File005.cif
_cod_data_source_block           25
_cod_database_code               4024184
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.51925(3) 0.79417(2) 0.292571(17) 0.01406(6) Uani 1 1 d . . .
S3 S 0.69740(3) 0.97375(3) 0.162754(17) 0.01494(6) Uani 1 1 d . . .
S2 S 0.52087(3) 1.07385(2) 0.304185(16) 0.01320(5) Uani 1 1 d . . .
N1 N 0.32222(12) 0.78032(10) 0.05187(6) 0.01844(16) Uani 1 1 d . . .
C21 C 0.95455(13) 1.22047(11) 0.29305(8) 0.01734(18) Uani 1 1 d . . .
H21 H 0.8929 1.2682 0.2490 0.021 Uiso 1 1 calc R . .
C9 C 0.31446(14) 0.77718(11) 0.42142(7) 0.01710(17) Uani 1 1 d . . .
H9 H 0.4265 0.8430 0.4697 0.021 Uiso 1 1 calc R . .
C8 C 0.31082(13) 0.73360(10) 0.32366(7) 0.01366(16) Uani 1 1 d . . .
C2 C 0.32281(12) 0.87132(10) 0.12426(7) 0.01322(16) Uani 1 1 d . . .
C3 C 0.16891(14) 0.90060(11) 0.12118(8) 0.01799(18) Uani 1 1 d . . .
H3 H 0.1743 0.9657 0.1740 0.022 Uiso 1 1 calc R . .
C20 C 0.89163(13) 1.07265(11) 0.27239(7) 0.01549(17) Uani 1 1 d . . .
C19 C 0.49258(13) 1.22287(10) 0.13650(7) 0.01535(17) Uani 1 1 d . . .
H19 H 0.4929 1.1473 0.0946 0.018 Uiso 1 1 calc R . .
C25 C 0.98439(14) 1.00297(12) 0.33628(8) 0.01973(19) Uani 1 1 d . . .
H25 H 0.9443 0.9028 0.3214 0.024 Uiso 1 1 calc R . .
C23 C 1.19683(14) 1.22761(12) 0.44292(8) 0.0211(2) Uani 1 1 d . . .
H23 H 1.2999 1.2802 0.5017 0.025 Uiso 1 1 calc R . .
C18 C 0.48196(14) 1.34332(11) 0.09684(8) 0.01761(18) Uani 1 1 d . . .
H18 H 0.4756 1.3493 0.0277 0.021 Uiso 1 1 calc R . .
C24 C 1.13619(14) 1.08105(12) 0.42209(8) 0.0222(2) Uani 1 1 d . . .
H24 H 1.1982 1.0338 0.4664 0.027 Uiso 1 1 calc R . .
C15 C 0.50165(14) 1.32656(10) 0.29912(8) 0.01683(17) Uani 1 1 d . . .
H15 H 0.5091 1.3215 0.3684 0.020 Uiso 1 1 calc R . .
C11 C -0.01079(15) 0.62929(12) 0.37707(8) 0.0212(2) Uani 1 1 d . . .
H11 H -0.1204 0.5939 0.3952 0.025 Uiso 1 1 calc R . .
C22 C 1.10750(14) 1.29792(12) 0.37818(8) 0.01987(19) Uani 1 1 d . . .
H22 H 1.1507 1.3984 0.3920 0.024 Uiso 1 1 calc R . .
C14 C 0.50275(12) 1.21456(10) 0.23824(7) 0.01291(16) Uani 1 1 d . . .
C12 C -0.01510(14) 0.58614(11) 0.27940(8) 0.02007(19) Uani 1 1 d . . .
H12 H -0.1281 0.5222 0.2308 0.024 Uiso 1 1 calc R . .
C13 C 0.14545(14) 0.63636(10) 0.25275(7) 0.01715(18) Uani 1 1 d . . .
H13 H 0.1429 0.6048 0.1867 0.021 Uiso 1 1 calc R . .
C4 C 0.00729(15) 0.83220(13) 0.03888(9) 0.0235(2) Uani 1 1 d . . .
H4 H -0.0999 0.8500 0.0344 0.028 Uiso 1 1 calc R . .
C10 C 0.15399(15) 0.72423(12) 0.44821(8) 0.0211(2) Uani 1 1 d . . .
H10 H 0.1570 0.7529 0.5150 0.025 Uiso 1 1 calc R . .
C6 C 0.16508(15) 0.71545(13) -0.02629(8) 0.0244(2) Uani 1 1 d . . .
H6 H 0.1630 0.6503 -0.0779 0.029 Uiso 1 1 calc R . .
C5 C 0.00493(15) 0.73777(14) -0.03640(8) 0.0261(2) Uani 1 1 d . . .
H5 H -0.1034 0.6895 -0.0935 0.031 Uiso 1 1 calc R . .
C16 C 0.48965(15) 1.44484(11) 0.25823(8) 0.01981(19) Uani 1 1 d . . .
H16 H 0.4876 1.5200 0.2997 0.024 Uiso 1 1 calc R . .
C17 C 0.48052(14) 1.45456(11) 0.15704(8) 0.01891(18) Uani 1 1 d . . .
H17 H 0.4734 1.5361 0.1295 0.023 Uiso 1 1 calc R . .
C7 C 0.50183(12) 0.93263(9) 0.21412(7) 0.01159(15) Uani 1 1 d . . .
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
C8 S1 C7 104.27(4) . . ?
C20 S3 C7 102.10(4) . . ?
C14 S2 C7 108.29(4) . . ?
C6 N1 C2 117.42(9) . . ?
C22 C21 C20 120.08(9) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C10 C9 C8 120.08(9) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C8 C13 119.79(9) . . ?
C9 C8 S1 119.68(7) . . ?
C13 C8 S1 120.43(7) . . ?
N1 C2 C3 123.09(9) . . ?
N1 C2 C7 114.21(8) . . ?
C3 C2 C7 122.57(8) . . ?
C4 C3 C2 118.40(10) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C25 C20 C21 119.87(9) . . ?
C25 C20 S3 120.03(8) . . ?
C21 C20 S3 120.07(7) . . ?
C14 C19 C18 119.40(9) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C24 C25 C20 119.73(10) . . ?
C24 C25 H25 120.1 . . ?
C20 C25 H25 120.1 . . ?
C24 C23 C22 120.34(10) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C17 C18 C19 120.98(9) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C23 C24 C25 120.16(10) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C16 C15 C14 120.05(9) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C11 C12 120.07(10) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C23 C22 C21 119.79(10) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C19 C14 C15 119.75(9) . . ?
C19 C14 S2 126.81(7) . . ?
C15 C14 S2 113.44(7) . . ?
C13 C12 C11 120.25(9) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 119.79(9) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C5 C4 C3 119.04(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C11 C10 C9 120.00(9) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
N1 C6 C5 123.82(10) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C4 C5 C6 118.23(10) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C15 C16 C17 120.66(9) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.15(9) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C2 C7 S2 115.52(6) . . ?
C2 C7 S1 109.67(6) . . ?
S2 C7 S1 103.35(4) . . ?
C2 C7 S3 107.86(6) . . ?
S2 C7 S3 115.25(5) . . ?
S1 C7 S3 104.44(4) . . ?
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
S1 C8 1.7792(10) . ?
S1 C7 1.8496(9) . ?
S3 C20 1.7815(10) . ?
S3 C7 1.8566(9) . ?
S2 C14 1.7727(9) . ?
S2 C7 1.8031(9) . ?
N1 C6 1.3376(13) . ?
N1 C2 1.3390(12) . ?
C21 C22 1.3926(14) . ?
C21 C20 1.3977(14) . ?
C21 H21 0.9500 . ?
C9 C10 1.3930(14) . ?
C9 C8 1.3968(13) . ?
C9 H9 0.9500 . ?
C8 C13 1.4006(13) . ?
C2 C3 1.3942(13) . ?
C2 C7 1.5215(12) . ?
C3 C4 1.3914(14) . ?
C3 H3 0.9500 . ?
C20 C25 1.3964(14) . ?
C19 C14 1.3965(13) . ?
C19 C18 1.3972(14) . ?
C19 H19 0.9500 . ?
C25 C24 1.3951(15) . ?
C25 H25 0.9500 . ?
C23 C24 1.3874(16) . ?
C23 C22 1.3918(15) . ?
C23 H23 0.9500 . ?
C18 C17 1.3911(15) . ?
C18 H18 0.9500 . ?
C24 H24 0.9500 . ?
C15 C16 1.3870(14) . ?
C15 C14 1.4013(13) . ?
C15 H15 0.9500 . ?
C11 C10 1.3918(14) . ?
C11 C12 1.3925(15) . ?
C11 H11 0.9500 . ?
C22 H22 0.9500 . ?
C12 C13 1.3914(15) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C4 C5 1.3844(17) . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?
C6 C5 1.3876(16) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C16 C17 1.3926(15) . ?
C16 H16 0.9500 . ?
C17 H17 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
C10 C9 C8 C13 -0.10(15) . . . . ?
C10 C9 C8 S1 -176.49(8) . . . . ?
C7 S1 C8 C9 -103.68(8) . . . . ?
C7 S1 C8 C13 79.96(8) . . . . ?
C6 N1 C2 C3 -0.11(15) . . . . ?
C6 N1 C2 C7 175.88(9) . . . . ?
N1 C2 C3 C4 -0.13(16) . . . . ?
C7 C2 C3 C4 -175.79(9) . . . . ?
C22 C21 C20 C25 -1.12(15) . . . . ?
C22 C21 C20 S3 -179.36(8) . . . . ?
C7 S3 C20 C25 90.97(9) . . . . ?
C7 S3 C20 C21 -90.79(8) . . . . ?
C21 C20 C25 C24 1.87(15) . . . . ?
S3 C20 C25 C24 -179.89(8) . . . . ?
C14 C19 C18 C17 -0.30(15) . . . . ?
C22 C23 C24 C25 -0.34(17) . . . . ?
C20 C25 C24 C23 -1.14(16) . . . . ?
C24 C23 C22 C21 1.09(16) . . . . ?
C20 C21 C22 C23 -0.36(15) . . . . ?
C18 C19 C14 C15 0.18(14) . . . . ?
C18 C19 C14 S2 -178.88(7) . . . . ?
C16 C15 C14 C19 0.29(15) . . . . ?
C16 C15 C14 S2 179.48(8) . . . . ?
C7 S2 C14 C19 -5.43(10) . . . . ?
C7 S2 C14 C15 175.45(7) . . . . ?
C10 C11 C12 C13 0.72(17) . . . . ?
C11 C12 C13 C8 -1.71(16) . . . . ?
C9 C8 C13 C12 1.40(15) . . . . ?
S1 C8 C13 C12 177.76(8) . . . . ?
C2 C3 C4 C5 0.18(16) . . . . ?
C12 C11 C10 C9 0.58(17) . . . . ?
C8 C9 C10 C11 -0.88(16) . . . . ?
C2 N1 C6 C5 0.32(17) . . . . ?
C3 C4 C5 C6 0.00(18) . . . . ?
N1 C6 C5 C4 -0.26(19) . . . . ?
C14 C15 C16 C17 -0.67(16) . . . . ?
C19 C18 C17 C16 -0.07(15) . . . . ?
C15 C16 C17 C18 0.55(16) . . . . ?
N1 C2 C7 S2 171.60(7) . . . . ?
C3 C2 C7 S2 -12.38(12) . . . . ?
N1 C2 C7 S1 -72.14(9) . . . . ?
C3 C2 C7 S1 103.88(9) . . . . ?
N1 C2 C7 S3 41.02(10) . . . . ?
C3 C2 C7 S3 -142.96(8) . . . . ?
C14 S2 C7 C2 -59.35(8) . . . . ?
C14 S2 C7 S1 -179.14(4) . . . . ?
C14 S2 C7 S3 67.58(6) . . . . ?
C8 S1 C7 C2 -55.05(7) . . . . ?
C8 S1 C7 S2 68.67(5) . . . . ?
C8 S1 C7 S3 -170.41(4) . . . . ?
C20 S3 C7 C2 169.76(6) . . . . ?
C20 S3 C7 S2 39.03(6) . . . . ?
C20 S3 C7 S1 -73.62(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658848
