#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/1100679.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_1100679
_chemical_formula_sum  'C14 H16 N2 S'
_chemical_formula_weight          244.35
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'
 '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'
_symmetry_cell_setting            ?
_symmetry_space_group_name_H-M    P-1
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
_cell_length_a                    10.4686(16)
_cell_length_b                    11.9543(16)
_cell_length_c                    5.9271(16)
_cell_angle_alpha                 102.365(16)
_cell_angle_beta                  92.120(16)
_cell_angle_gamma                 65.302(15)
_cell_volume                      657.1(2)
_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        'prism'
_exptl_crystal_colour             'colorless'
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.30
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.235
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              260
_exptl_absorpt_coefficient_mu     0.226
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_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             4029
_diffrn_reflns_av_R_equivalents   0.0101
_diffrn_reflns_av_sigmaI/netI     0.0222
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_theta_min          2.14
_diffrn_reflns_theta_max          30.00
_reflns_number_total              3836
_reflns_number_gt                 2561
_reflns_threshold_expression      >2sigma(I)
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme
 'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.1601P] 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      SHELXL
_refine_ls_extinction_coef        0.027(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          3836
_refine_ls_number_parameters      156
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0727
_refine_ls_R_factor_gt            0.0419
_refine_ls_wR_factor_ref          0.1333
_refine_ls_wR_factor_gt           0.1149
_refine_ls_goodness_of_fit_ref    1.050
_refine_ls_restrained_S_all       1.050
_refine_ls_shift/su_max           0.000
_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
S1 S 0.29613(5) 0.29883(4) 1.02974(10) 0.06480(18) Uani 1 d . . .
N1 N 0.51156(16) 0.36496(15) 1.1237(3) 0.0718(5) Uani 1 d . . .
H1A H 0.5563 0.4107 1.1190 0.086 Uiso 1 calc R . .
H1B H 0.5459 0.3029 1.1922 0.086 Uiso 1 calc R . .
N2 N 0.32819(13) 0.48227(12) 0.9170(2) 0.0460(3) Uani 1 d . . ..
C1 C 0.38836(16) 0.39043(14) 1.0244(3) 0.0498(4) Uani 1 d . . .
C2 C 0.16829(19) 0.39381(16) 0.8776(4) 0.0584(4) Uani 1 d . . .
H2 H 0.0873 0.3835 0.8317 0.070 Uiso 1 calc R . .
C3 C 0.20124(16) 0.48482(15) 0.8341(3) 0.0462(3) Uani 1 d . . ..
C4 C 0.11132(16) 0.58942(15) 0.7207(3) 0.0473(4) Uani 1 d . . .
H4 H 0.0238 0.5820 0.6749 0.057 Uiso 1 calc R . .
C5 C 0.07999(17) 0.72492(14) 0.8578(3) 0.0462(3) Uani 1 d . . .
H5A H -0.0166 0.7727 0.9204 0.055 Uiso 1 calc R . ..
H5B H 0.1455 0.7280 0.9765 0.055 Uiso 1 calc R . .
C6 C 0.17879(18) 0.61554(15) 0.5214(3) 0.0504(4) Uani 1 d . . .
H6A H 0.1446 0.5944 0.3711 0.061 Uiso 1 calc R . .
H6B H 0.2809 0.5781 0.5152 0.061 Uiso 1 calc R . .
C7 C 0.11056(16) 0.75928(15) 0.6341(3) 0.0453(3) Uani 1 d . . ..
C8 C -0.0263(2) 0.83151(19) 0.5245(3) 0.0617(5) Uani 1 d . . .
H8A H -0.0732 0.9155 0.6170 0.093 Uiso 1 calc R . .
H8B H -0.0867 0.7887 0.5168 0.093 Uiso 1 calc R . .
H8C H -0.0046 0.8355 0.3712 0.093 Uiso 1 calc R . .
C9 C 0.20555(17) 0.82621(14) 0.6526(3) 0.0470(3) Uani 1 d . . ..
C10 C 0.3009(2) 0.80162(19) 0.4722(3) 0.0643(5) Uani 1 d . . .
H10 H 0.3048 0.7441 0.3363 0.077 Uiso 1 calc R . .
C11 C 0.3900(3) 0.8611(2) 0.4910(4) 0.0805(6) Uani 1 d . . .
H11 H 0.4528 0.8438 0.3678 0.097 Uiso 1 calc R . .
C12 C 0.3867(2) 0.9463(2) 0.6915(5) 0.0784(6) Uani 1 d .. . .
H12 H 0.4481 0.9851 0.7049 0.094 Uiso 1 calc R . .
C13 C 0.2918(2) 0.97311(18) 0.8709(4) 0.0672(5) Uani 1 d . . .
H13 H 0.2877 1.0316 1.0054 0.081 Uiso 1 calc R . .
C14 C 0.20254(18) 0.91343(15) 0.8520(3) 0.0539(4) Uani 1 d . . ..
H14 H 0.1392 0.9320 0.9751 0.065 Uiso 1 calc R . .
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
S1 0.0585(3) 0.0459(2) 0.1010(4) 0.0248(2) -0.0051(2) -0.0283(2)
N1 0.0525(9) 0.0640(9) 0.1174(15) 0.0512(10) -0.0285(9) -0.0291(7)
N2 0.0397(6) 0.0429(6) 0.0606(8) 0.0152(6) -0.0074(6) -0.0209(5)
C1 0.0429(8) 0.0412(7) 0.0676(10) 0.0149(7) -0.0023(7) -0.0185(6)
C2 0.0502(9) 0.0502(9) 0.0815(13) 0.0107(8) -0.0076(8) -0.0296(8)
C3 0.0423(7) 0.0431(7) 0.0548(9) 0.0067(6) -0.0043(6) -0.0215(6)
C4 0.0423(8) 0.0507(8) 0.0497(9) 0.0086(7) -0.0097(6) -0.0220(7)
C5 0.0449(8) 0.0473(8) 0.0420(8) 0.0077(6) -0.0048(6) -0.0163(6)
C6 0.0534(9) 0.0509(8) 0.0407(8) 0.0029(6) -0.0057(7) -0.0195(7)
C7 0.0461(8) 0.0463(8) 0.0380(7) 0.0086(6) -0.0086(6) -0.0147(6)
C8 0.0560(10) 0.0656(11) 0.0540(10) 0.0158(8) -0.0183(8) -0.0163(8)
C9 0.0474(8) 0.0437(8) 0.0474(8) 0.0158(6) -0.0076(6) -0.0143(6)
C10 0.0747(13) 0.0712(12) 0.0520(10) 0.0165(9) 0.0029(9) -0.0334(10)
C11 0.0866(16) 0.0885(15) 0.0811(15) 0.0281(13) 0.0114(12) -0.0449(13)
C12 0.0787(14) 0.0713(13) 0.1046(18) 0.0322(13) -0.0070(13) -0.0441(12)
C13 0.0719(12) 0.0494(9) 0.0827(14) 0.0125(9) -0.0090(10) -0.0290(9)
C14 0.0534(9) 0.0448(8) 0.0586(10) 0.0079(7) -0.0033(8) -0.0174(7)
_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
S1 C2 1.724(2) . ?
S1 C1 1.7415(16) . ?
N1 C1 1.340(2) . ?
N2 C1 1.304(2) . ?
N2 C3 1.3903(19) . ?
C2 C3 1.345(2) . ?
C3 C4 1.493(2) . ?
C4 C6 1.548(2) . ?
C4 C5 1.550(2) . ?
C5 C7 1.550(2) . ?
C6 C7 1.558(2) . ?
C7 C9 1.503(2) . ?
C7 C8 1.536(2) . ?
C9 C10 1.388(2) . ?
C9 C14 1.390(2) . ?
C10 C11 1.379(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.373(3) . ?
C13 C14 1.382(3) . ?
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
C2 S1 C1 88.57(8) . . ?
C1 N2 C3 110.78(13) . . ?
N2 C1 N1 124.35(15) . . ?
N2 C1 S1 114.67(12) . . ?
N1 C1 S1 120.98(12) . . ?
C3 C2 S1 111.04(13) . . ?
C2 C3 N2 114.94(15) . . ?
C2 C3 C4 126.19(15) . . ?
N2 C3 C4 118.76(13) . . ?
C3 C4 C6 118.51(14) . . ?
C3 C4 C5 116.02(13) . . ?
C6 C4 C5 88.33(12) . . ?
C7 C5 C4 90.16(12) . . ?
C4 C6 C7 89.95(12) . . ?
C9 C7 C8 110.40(14) .. . ?
C9 C7 C5 116.61(12) . . ?
C8 C7 C5 111.35(14) . . ?
C9 C7 C6 116.26(13) . . ?
C8 C7 C6 112.63(13) . . ?
C5 C7 C6 87.99(12) . . ?
C10 C9 C14 117.64(17) . . ?
C10 C9 C7 121.08(16) . . ?
C14 C9 C7 121.27(15) . . ?
C11 C10 C9 121.1(2) . . ?
C10 C11 C12 120.5(2) . . ?
C13 C12 C11 119.3(2) . . ?
C12 C13 C14 120.2(2) . . ?
C13 C14 C9 121.29(18) . . ?
_diffrn_measured_fraction_theta_max    1.000
_diffrn_reflns_theta_full              30.00
_diffrn_measured_fraction_theta_full   1.000
_refine_diff_density_max    0.224
_refine_diff_density_min   -0.262
_refine_diff_density_rms    0.037