Douglas X. West
Department of Chemistry, 351700
University of Washington
Seattle, WA 98195-1700

data_shelxl 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic  N-2-(6-picolyl)-N'-4-tolylthiourea
_chemical_name_common             6PicTu4T 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C14 H15 N3 S' 
_chemical_formula_weight          257.35 
 
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' 
 'S'  'S'   0.1246   0.1234 
 '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' 
 
_symmetry_cell_setting            ? 
_symmetry_space_group_name_H-M    ? 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    8.829(6) 
_cell_length_b                    8.9850(15) 
_cell_length_c                    10.495(3) 
_cell_angle_alpha                 68.63(3) 
_cell_angle_beta                  72.19(4) 
_cell_angle_gamma                 63.06(4) 
_cell_volume                      681.2(5) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.255 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              272 
_exptl_absorpt_coefficient_mu     0.223 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.70930 
_diffrn_radiation_type            ? 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             3307 
_diffrn_reflns_av_R_equivalents   0.0270 
_diffrn_reflns_av_sigmaI/netI     0.0140 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          2.11 
_diffrn_reflns_theta_max          27.41 
_reflns_number_total              3104 
_reflns_number_gt                 2494 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
 'calc w=1/[\s^2^(Fo^2^)+(0.0702P)^2^+0.1119P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3104 
_refine_ls_number_parameters      201 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0554 
_refine_ls_R_factor_gt            0.0420 
_refine_ls_wR_factor_ref          0.1364 
_refine_ls_wR_factor_gt           0.1186 
_refine_ls_goodness_of_fit_ref    1.105 
_refine_ls_restrained_S_all       1.105 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
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_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C2 C 0.11103(19) 0.14691(19) 0.88942(16) 0.0506(3) Uani 1 d . . . 
C3 C 0.0090(2) 0.2310(2) 0.78559(19) 0.0627(4) Uani 1 d . . . 
H3 H -0.061(3) 0.346(3) 0.772(2) 0.082(6) Uiso 1 d . . . 
C4 C 0.0221(3) 0.1363(3) 0.7031(2) 0.0696(5) Uani 1 d . . . 
H4 H -0.044(3) 0.186(3) 0.636(2) 0.085(7) Uiso 1 d . . . 
C5 C 0.1333(3) -0.0348(3) 0.7223(2) 0.0688(5) Uani 1 d . . . 
H5 H 0.140(3) -0.101(3) 0.672(2) 0.078(6) Uiso 1 d . . . 
C6 C 0.2310(2) -0.1098(2) 0.82705(18) 0.0596(4) Uani 1 d . . . 
C7 C 0.1804(2) 0.18656(19) 1.08816(16) 0.0514(3) Uani 1 d . . . 
C8 C 0.38887(19) -0.08306(18) 1.22477(15) 0.0493(3) Uani 1 d . . . 
C9 C 0.3736(3) -0.0429(2) 1.34443(19) 0.0711(5) Uani 1 d . . . 
H9 H 0.292(3) 0.057(3) 1.364(2) 0.086(7) Uiso 1 d . . . 
C10 C 0.4830(3) -0.1596(3) 1.4394(2) 0.0754(5) Uani 1 d . . . 
H10 H 0.470(3) -0.131(3) 1.522(3) 0.089(7) Uiso 1 d . . . 
C11 C 0.6066(2) -0.3164(2) 1.41940(18) 0.0622(4) Uani 1 d . . . 
C12 C 0.6188(2) -0.3560(2) 1.3006(2) 0.0650(4) Uani 1 d . . . 
H12 H 0.704(3) -0.471(3) 1.284(2) 0.089(7) Uiso 1 d . . . 
C13 C 0.5112(2) -0.2420(2) 1.20424(18) 0.0573(4) Uani 1 d . . . 
H13 H 0.515(3) -0.264(3) 1.119(3) 0.085(6) Uiso 1 d . . . 
C14 C 0.3545(3) -0.2952(3) 0.8580(3) 0.0839(6) Uani 1 d . . . 
H14A H 0.4649 -0.3010 0.8603 0.126 Uiso 1 calc R . . 
H14B H 0.3661 -0.3452 0.7871 0.126 Uiso 1 calc R . . 
H14C H 0.3116 -0.3582 0.9464 0.126 Uiso 1 calc R . . 
C15 C 0.7262(3) -0.4402(3) 1.5230(2) 0.0867(7) Uani 1 d . . . 
H15A H 0.7437 -0.3758 1.5690 0.130 Uiso 1 calc R . . 
H15B H 0.8349 -0.5048 1.4754 0.130 Uiso 1 calc R . . 
H15C H 0.6758 -0.5185 1.5904 0.130 Uiso 1 calc R . . 
N1 N 0.21913(17) -0.01833(17) 0.90918(13) 0.0534(3) Uani 1 d . . . 
N2 N 0.09984(18) 0.23923(18) 0.97715(14) 0.0552(3) Uani 1 d . . . 
H2 H 0.039(2) 0.339(3) 0.9566(19) 0.055(5) Uiso 1 d . . . 
N3 N 0.28754(17) 0.02041(17) 1.11867(14) 0.0529(3) Uani 1 d . . . 
H3A H 0.291(2) -0.032(3) 1.067(2) 0.061(5) Uiso 1 d . . . 
S1 S 0.13679(7) 0.33445(6) 1.17115(5) 0.0774(2) Uani 1 d . . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
C2 0.0517(8) 0.0439(7) 0.0526(7) -0.0070(6) -0.0151(6) -0.0158(6) 
C3 0.0668(10) 0.0505(9) 0.0694(10) -0.0062(7) -0.0307(8) -0.0167(8) 
C4 0.0785(12) 0.0667(11) 0.0708(10) -0.0087(9) -0.0374(9) -0.0259(9) 
C5 0.0797(12) 0.0665(11) 0.0718(11) -0.0217(9) -0.0255(9) -0.0274(9) 
C6 0.0631(9) 0.0536(9) 0.0627(9) -0.0188(7) -0.0150(7) -0.0177(7) 
C7 0.0522(8) 0.0401(7) 0.0548(8) -0.0097(6) -0.0167(6) -0.0093(6) 
C8 0.0495(7) 0.0416(7) 0.0503(7) -0.0066(6) -0.0162(6) -0.0116(6) 
C9 0.0797(12) 0.0550(10) 0.0612(10) -0.0197(8) -0.0266(8) 0.0012(9) 
C10 0.0921(14) 0.0670(11) 0.0580(10) -0.0156(8) -0.0324(9) -0.0113(10) 
C11 0.0585(9) 0.0568(9) 0.0633(9) 0.0004(7) -0.0252(7) -0.0189(7) 
C12 0.0593(9) 0.0478(8) 0.0743(11) -0.0114(8) -0.0244(8) -0.0049(7) 
C13 0.0592(9) 0.0451(8) 0.0635(9) -0.0152(7) -0.0218(7) -0.0088(7) 
C14 0.0956(15) 0.0578(10) 0.0972(15) -0.0338(10) -0.0345(12) -0.0071(10) 
C15 0.0791(13) 0.0818(14) 0.0799(13) 0.0032(11) -0.0411(11) -0.0163(11) 
N1 0.0558(7) 0.0455(7) 0.0551(7) -0.0122(5) -0.0163(5) -0.0129(5) 
N2 0.0598(7) 0.0377(6) 0.0599(7) -0.0102(5) -0.0243(6) -0.0053(6) 
N3 0.0569(7) 0.0412(6) 0.0542(7) -0.0129(5) -0.0212(6) -0.0060(5) 
S1 0.1003(4) 0.0446(3) 0.0852(4) -0.0223(2) -0.0494(3) -0.0011(2) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
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 
C2 N1 1.331(2) . ? 
C2 C3 1.398(2) . ? 
C2 N2 1.404(2) . ? 
C3 C4 1.369(3) . ? 
C3 H3 0.92(2) . ? 
C4 C5 1.377(3) . ? 
C4 H4 0.91(2) . ? 
C5 C6 1.385(3) . ? 
C5 H5 0.90(2) . ? 
C6 N1 1.346(2) . ? 
C6 C14 1.499(3) . ? 
C7 N3 1.336(2) . ? 
C7 N2 1.374(2) . ? 
C7 S1 1.6875(17) . ? 
C8 C9 1.381(2) . ? 
C8 C13 1.391(2) . ? 
C8 N3 1.416(2) . ? 
C9 C10 1.391(3) . ? 
C9 H9 0.91(2) . ? 
C10 C11 1.379(3) . ? 
C10 H10 0.95(2) . ? 
C11 C12 1.378(3) . ? 
C11 C15 1.514(2) . ? 
C12 C13 1.388(2) . ? 
C12 H12 1.00(2) . ? 
C13 H13 0.97(2) . ? 
C14 H14A 0.9600 . ? 
C14 H14B 0.9600 . ? 
C14 H14C 0.9600 . ? 
C15 H15A 0.9600 . ? 
C15 H15B 0.9600 . ? 
C15 H15C 0.9600 . ? 
N2 H2 0.80(2) . ? 
N3 H3A 0.83(2) . ? 
 
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 
N1 C2 C3 122.64(15) . . ? 
N1 C2 N2 118.18(13) . . ? 
C3 C2 N2 119.18(15) . . ? 
C4 C3 C2 117.50(17) . . ? 
C4 C3 H3 121.6(14) . . ? 
C2 C3 H3 120.9(14) . . ? 
C3 C4 C5 120.49(17) . . ? 
C3 C4 H4 119.7(15) . . ? 
C5 C4 H4 119.8(15) . . ? 
C4 C5 C6 118.93(18) . . ? 
C4 C5 H5 122.0(14) . . ? 
C6 C5 H5 119.0(14) . . ? 
N1 C6 C5 121.21(16) . . ? 
N1 C6 C14 115.46(16) . . ? 
C5 C6 C14 123.33(17) . . ? 
N3 C7 N2 115.39(14) . . ? 
N3 C7 S1 126.59(12) . . ? 
N2 C7 S1 118.02(12) . . ? 
C9 C8 C13 118.78(15) . . ? 
C9 C8 N3 126.52(14) . . ? 
C13 C8 N3 114.67(14) . . ? 
C8 C9 C10 119.51(17) . . ? 
C8 C9 H9 121.6(15) . . ? 
C10 C9 H9 118.9(15) . . ? 
C11 C10 C9 122.33(18) . . ? 
C11 C10 H10 119.1(15) . . ? 
C9 C10 H10 118.5(15) . . ? 
C12 C11 C10 117.58(16) . . ? 
C12 C11 C15 120.99(18) . . ? 
C10 C11 C15 121.43(19) . . ? 
C11 C12 C13 121.25(17) . . ? 
C11 C12 H12 120.1(14) . . ? 
C13 C12 H12 118.6(14) . . ? 
C12 C13 C8 120.53(17) . . ? 
C12 C13 H13 124.2(14) . . ? 
C8 C13 H13 115.2(14) . . ? 
C6 C14 H14A 109.5 . . ? 
C6 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C6 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C11 C15 H15A 109.5 . . ? 
C11 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C11 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
C2 N1 C6 119.23(14) . . ? 
C7 N2 C2 130.65(13) . . ? 
C7 N2 H2 115.7(14) . . ? 
C2 N2 H2 113.7(14) . . ? 
C7 N3 C8 132.72(14) . . ? 
C7 N3 H3A 112.5(14) . . ? 
C8 N3 H3A 114.7(14) . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N3 H3A N1  0.83(2) 1.89(2) 2.623(2) 146.9(19) . 
N2 H2 S1  0.80(2) 2.66(2) 3.443(2) 166.8(17) 2_567 
C3 H3 S1  0.92(2) 2.88(2) 3.673(2) 145.2(18) 2_567 
 
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              27.41 
_diffrn_measured_fraction_theta_full   0.996 
_refine_diff_density_max    0.240 
_refine_diff_density_min   -0.199 
_refine_diff_density_rms    0.037