data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. C. Gabbutt
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H13 N O3 S'
_chemical_formula_sum
 'C14 H13 N O3 S'
_chemical_formula_weight          275.31
 
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    P2(1)/n
_symmetry_space_group_name_hall   '-P 2yn'
 
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'
 
_cell_length_a                    9.8330(2)
_cell_length_b                    9.9814(3)
_cell_length_c                    13.8500(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  108.9040(10)
_cell_angle_gamma                 90.00
_cell_volume                      1286.02(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3008
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Shard
_exptl_crystal_colour             'Light Yellow'
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.422
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              576
_exptl_absorpt_coefficient_mu     0.254
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9276
_exptl_absorpt_correction_T_max   0.9924
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             15072
_diffrn_reflns_av_R_equivalents   0.0497
_diffrn_reflns_av_sigmaI/netI     0.0395
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          2.99
_diffrn_reflns_theta_max          27.45
_reflns_number_total              2928
_reflns_number_gt                 2495
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_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)+(0.0353P)²+1.0653P] 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      SHELXL
_refine_ls_extinction_coef        0.0079(19)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2928
_refine_ls_number_parameters      175
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0504
_refine_ls_R_factor_gt            0.0409
_refine_ls_wR_factor_ref          0.1035
_refine_ls_wR_factor_gt           0.0982
_refine_ls_goodness_of_fit_ref    1.069
_refine_ls_restrained_S_all       1.069
_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_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.94178(19) 0.35626(19) 0.06177(15) 0.0241(4) Uani 1 1 d . . .
H1 H 1.0233 0.3179 0.1112 0.029 Uiso 1 1 calc R . .
C2 C 0.90668(19) 0.33461(19) -0.04071(15) 0.0241(4) Uani 1 1 d . . .
H2 H 0.9617 0.2793 -0.0699 0.029 Uiso 1 1 calc R . .
C3 C 0.77958(17) 0.40300(17) -0.09979(13) 0.0172(3) Uani 1 1 d . . .
H3 H 0.7396 0.3990 -0.1720 0.021 Uiso 1 1 calc R . .
C4 C 0.72182(17) 0.47732(17) -0.03568(12) 0.0172(4) Uani 1 1 d . . .
C5 C 0.60236(17) 0.57345(17) -0.06462(12) 0.0164(3) Uani 1 1 d . . .
C6 C 0.49693(17) 0.56505(17) -0.17080(12) 0.0158(3) Uani 1 1 d . . .
C7 C 0.43676(18) 0.44224(18) -0.21092(13) 0.0190(4) Uani 1 1 d . . .
H7 H 0.4693 0.3625 -0.1730 0.023 Uiso 1 1 calc R . .
C8 C 0.32956(19) 0.43487(19) -0.30582(14) 0.0220(4) Uani 1 1 d . . .
H8 H 0.2886 0.3509 -0.3320 0.026 Uiso 1 1 calc R . .
C9 C 0.28322(18) 0.5514(2) -0.36170(13) 0.0226(4) Uani 1 1 d . . .
H9 H 0.2101 0.5469 -0.4263 0.027 Uiso 1 1 calc R . .
C10 C 0.34298(18) 0.67421(19) -0.32384(13) 0.0205(4) Uani 1 1 d . . .
H10 H 0.3115 0.7536 -0.3624 0.025 Uiso 1 1 calc R . .
C11 C 0.44895(17) 0.68024(17) -0.22936(13) 0.0170(3) Uani 1 1 d . . .
C12 C 0.64600(17) 0.82903(17) -0.17343(12) 0.0168(3) Uani 1 1 d . . .
C13 C 0.5816(2) 1.06206(19) -0.14315(16) 0.0274(4) Uani 1 1 d . . .
H13A H 0.4833 1.0272 -0.1691 0.041 Uiso 1 1 calc R . .
H13B H 0.5931 1.1348 -0.1874 0.041 Uiso 1 1 calc R . .
H13C H 0.6005 1.0962 -0.0737 0.041 Uiso 1 1 calc R . .
C14 C 0.83329(19) 0.9948(2) -0.11512(15) 0.0248(4) Uani 1 1 d . . .
H14A H 0.8929 0.9152 -0.1117 0.037 Uiso 1 1 calc R . .
H14B H 0.8630 1.0396 -0.0486 0.037 Uiso 1 1 calc R . .
H14C H 0.8450 1.0564 -0.1670 0.037 Uiso 1 1 calc R . .
N1 N 0.68282(15) 0.95509(15) -0.14205(11) 0.0201(3) Uani 1 1 d . . .
O1 O 0.58747(13) 0.65703(13) -0.00403(9) 0.0212(3) Uani 1 1 d . . .
O2 O 0.50108(12) 0.80823(12) -0.19494(9) 0.0191(3) Uani 1 1 d . . .
O3 O 0.72725(12) 0.74178(12) -0.18314(9) 0.0211(3) Uani 1 1 d . . .
S1 S 0.82328(5) 0.45949(5) 0.09099(3) 0.02332(15) 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 C2 1.365(3) . ?
C1 S1 1.6995(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.426(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.468(2) . ?
C4 S1 1.7235(17) . ?
C5 O1 1.225(2) . ?
C5 C6 1.502(2) . ?
C6 C7 1.396(2) . ?
C6 C11 1.398(2) . ?
C7 C8 1.395(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 O2 1.401(2) . ?
C12 O3 1.218(2) . ?
C12 N1 1.342(2) . ?
C12 O2 1.3739(19) . ?
C13 N1 1.456(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N1 1.459(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
 
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 C1 S1 112.44(14) . . ?
C2 C1 H1 123.8 . . ?
S1 C1 H1 123.8 . . ?
C1 C2 C3 113.59(17) . . ?
C1 C2 H2 123.2 . . ?
C3 C2 H2 123.2 . . ?
C4 C3 C2 110.32(15) . . ?
C4 C3 H3 124.8 . . ?
C2 C3 H3 124.8 . . ?
C3 C4 C5 128.44(15) . . ?
C3 C4 S1 111.61(12) . . ?
C5 C4 S1 119.56(13) . . ?
O1 C5 C4 121.37(15) . . ?
O1 C5 C6 120.72(15) . . ?
C4 C5 C6 117.91(14) . . ?
C7 C6 C11 118.13(15) . . ?
C7 C6 C5 120.52(15) . . ?
C11 C6 C5 121.21(15) . . ?
C8 C7 C6 120.98(17) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 119.47(17) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.46(16) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.51(17) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C6 121.44(16) . . ?
C10 C11 O2 116.19(15) . . ?
C6 C11 O2 122.34(14) . . ?
O3 C12 N1 126.03(16) . . ?
O3 C12 O2 122.63(15) . . ?
N1 C12 O2 111.34(14) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 N1 C13 124.92(15) . . ?
C12 N1 C14 118.85(15) . . ?
C13 N1 C14 115.86(15) . . ?
C12 O2 C11 116.80(13) . . ?
C1 S1 C4 92.04(9) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.45
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.397
_refine_diff_density_min   -0.371
_refine_diff_density_rms    0.062
