data_2005src0579
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C18 H18 N2 O S'
_chemical_formula_sum
 'C18 H18 N2 O S'
_chemical_formula_weight          310.40
 
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'
 'O'  'O'   0.0106   0.0060
 '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            Monoclinic
_symmetry_space_group_name_H-M    C2/c
_symmetry_space_group_name_hall   '-C 2yc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    34.115(7)
_cell_length_b                    5.1331(10)
_cell_length_c                    17.714(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  95.69(3)
_cell_angle_gamma                 90.00
_cell_volume                      3086.7(11)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3305
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        blade
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.336
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1312
_exptl_absorpt_coefficient_mu     0.213
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9010
_exptl_absorpt_correction_T_max   0.9979
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             10879
_diffrn_reflns_av_R_equivalents   0.1116
_diffrn_reflns_av_sigmaI/netI     0.1569
_diffrn_reflns_limit_h_min        -38
_diffrn_reflns_limit_h_max        44
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.60
_diffrn_reflns_theta_max          27.50
_reflns_number_total              3525
_reflns_number_gt                 1936
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0570P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3525
_refine_ls_number_parameters      202
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1588
_refine_ls_R_factor_gt            0.0756
_refine_ls_wR_factor_ref          0.1513
_refine_ls_wR_factor_gt           0.1240
_refine_ls_goodness_of_fit_ref    1.017
_refine_ls_restrained_S_all       1.017
_refine_ls_shift/su_max           0.002
_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_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.07615(9) 0.2612(5) 0.82849(18) 0.0183(7) Uani 1 1 d . . .
C2 C 0.08272(10) 0.4228(6) 0.8915(2) 0.0254(8) Uani 1 1 d . . .
H2 H 0.1045 0.5394 0.8951 0.031 Uiso 1 1 calc R . .
C3 C 0.05810(10) 0.4163(6) 0.9488(2) 0.0290(9) Uani 1 1 d . . .
H3 H 0.0629 0.5282 0.9915 0.035 Uiso 1 1 calc R . .
C4 C 0.02639(10) 0.2469(6) 0.9443(2) 0.0298(8) Uani 1 1 d . . .
H4 H 0.0093 0.2420 0.9836 0.036 Uiso 1 1 calc R . .
C5 C 0.01986(10) 0.0857(6) 0.8824(2) 0.0325(9) Uani 1 1 d . . .
H5 H -0.0019 -0.0310 0.8789 0.039 Uiso 1 1 calc R . .
C6 C 0.04447(10) 0.0917(6) 0.8253(2) 0.0278(9) Uani 1 1 d . . .
H6 H 0.0396 -0.0222 0.7831 0.033 Uiso 1 1 calc R . .
C7 C 0.10415(9) 0.2670(5) 0.76761(19) 0.0195(7) Uani 1 1 d . . .
H7 H 0.0956 0.1330 0.7284 0.023 Uiso 1 1 calc R . .
C8 C 0.10358(9) 0.5375(5) 0.72901(19) 0.0186(7) Uani 1 1 d . . .
H8 H 0.1045 0.6736 0.7695 0.022 Uiso 1 1 calc R . .
C9 C 0.06550(9) 0.5726(6) 0.6775(2) 0.0265(8) Uani 1 1 d . . .
H9A H 0.0651 0.7465 0.6546 0.040 Uiso 1 1 calc R . .
H9B H 0.0430 0.5535 0.7073 0.040 Uiso 1 1 calc R . .
H9C H 0.0640 0.4404 0.6374 0.040 Uiso 1 1 calc R . .
C10 C 0.13921(9) 0.5707(5) 0.68654(18) 0.0162(7) Uani 1 1 d . . .
C11 C 0.17370(9) 0.4158(5) 0.59164(18) 0.0173(7) Uani 1 1 d . . .
C12 C 0.13436(9) 0.0237(6) 0.5085(2) 0.0260(8) Uani 1 1 d . . .
H12A H 0.1333 -0.0644 0.5573 0.039 Uiso 1 1 calc R . .
H12B H 0.1350 -0.1065 0.4681 0.039 Uiso 1 1 calc R . .
H12C H 0.1110 0.1343 0.4981 0.039 Uiso 1 1 calc R . .
C13 C 0.20485(9) 0.5921(5) 0.61395(18) 0.0165(7) Uani 1 1 d . . .
C14 C 0.24109(9) 0.5983(6) 0.58304(19) 0.0214(8) Uani 1 1 d . . .
H14 H 0.2465 0.4747 0.5455 0.026 Uiso 1 1 calc R . .
C15 C 0.26892(9) 0.7830(6) 0.60690(19) 0.0219(8) Uani 1 1 d . . .
H15 H 0.2936 0.7849 0.5864 0.026 Uiso 1 1 calc R . .
C16 C 0.26072(9) 0.9679(6) 0.66138(19) 0.0207(8) Uani 1 1 d . . .
H16 H 0.2796 1.0986 0.6763 0.025 Uiso 1 1 calc R . .
C17 C 0.22600(9) 0.9624(5) 0.69316(19) 0.0190(7) Uani 1 1 d . . .
H17 H 0.2210 1.0878 0.7305 0.023 Uiso 1 1 calc R . .
C18 C 0.19749(9) 0.7723(5) 0.67101(17) 0.0168(7) Uani 1 1 d . . .
N1 N 0.14191(7) 0.4010(4) 0.62750(15) 0.0184(6) Uani 1 1 d . . .
N2 N 0.16387(7) 0.7589(4) 0.70755(15) 0.0178(6) Uani 1 1 d . . .
O1 O 0.14283(6) 0.2036(4) 0.80029(13) 0.0228(5) Uani 1 1 d . . .
H1 H 0.1513 0.0748 0.7775 0.034 Uiso 1 1 calc R . .
S1 S 0.17796(2) 0.22147(14) 0.51191(5) 0.0227(2) Uani 1 1 d . . .
 
 
_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
C1 C6 1.385(4) . ?
C1 C2 1.390(4) . ?
C1 C7 1.510(4) . ?
C2 C3 1.382(5) . ?
C3 C4 1.384(5) . ?
C4 C5 1.375(5) . ?
C5 C6 1.377(5) . ?
C7 O1 1.425(4) . ?
C7 C8 1.547(4) . ?
C8 C10 1.501(4) . ?
C8 C9 1.523(5) . ?
C10 N2 1.311(4) . ?
C10 N1 1.371(4) . ?
C11 N1 1.312(4) . ?
C11 C13 1.422(4) . ?
C11 S1 1.747(3) . ?
C12 S1 1.797(3) . ?
C13 C14 1.401(4) . ?
C13 C18 1.411(4) . ?
C14 C15 1.378(4) . ?
C15 C16 1.401(4) . ?
C16 C17 1.361(4) . ?
C17 C18 1.406(4) . ?
C18 N2 1.373(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
C6 C1 C2 118.1(3) . . ?
C6 C1 C7 122.0(3) . . ?
C2 C1 C7 119.9(3) . . ?
C3 C2 C1 120.9(3) . . ?
C2 C3 C4 120.1(3) . . ?
C5 C4 C3 119.2(3) . . ?
C4 C5 C6 120.7(3) . . ?
C5 C6 C1 120.9(3) . . ?
O1 C7 C1 109.3(3) . . ?
O1 C7 C8 110.8(2) . . ?
C1 C7 C8 110.6(2) . . ?
C10 C8 C9 111.8(3) . . ?
C10 C8 C7 110.4(2) . . ?
C9 C8 C7 110.1(2) . . ?
N2 C10 N1 126.5(3) . . ?
N2 C10 C8 118.0(3) . . ?
N1 C10 C8 115.4(3) . . ?
N1 C11 C13 122.2(3) . . ?
N1 C11 S1 119.8(2) . . ?
C13 C11 S1 117.9(2) . . ?
C14 C13 C18 119.5(3) . . ?
C14 C13 C11 124.7(3) . . ?
C18 C13 C11 115.8(3) . . ?
C15 C14 C13 120.2(3) . . ?
C14 C15 C16 119.9(3) . . ?
C17 C16 C15 120.8(3) . . ?
C16 C17 C18 120.3(3) . . ?
N2 C18 C17 119.3(3) . . ?
N2 C18 C13 121.4(3) . . ?
C17 C18 C13 119.2(3) . . ?
C11 N1 C10 117.0(3) . . ?
C10 N2 C18 116.4(2) . . ?
C11 S1 C12 102.43(16) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.288
_refine_diff_density_min   -0.288
_refine_diff_density_rms    0.079
