 
data_1
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C15 H11 N O2 S '
_chemical_formula_sum             'C15 H11 N O2 S' 
_chemical_formula_weight        269.31

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_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                    14.061(19)
_cell_length_b                    4.730(6)
_cell_length_c                    19.56(3)
_cell_angle_alpha                 90
_cell_angle_beta                  106.578(17)
_cell_angle_gamma                 90
_cell_volume                      1247(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     2151
_cell_measurement_theta_min       3.0231
_cell_measurement_theta_max       24.7510
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.435          
_exptl_crystal_F_000              560
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.030
_exptl_crystal_size_mid           0.020
_exptl_crystal_size_min           0.020
_exptl_absorpt_coefficient_mu     0.255
_shelx_estimated_absorpt_T_min    0.992
_shelx_estimated_absorpt_T_max    0.995
_exptl_absorpt_correction_type    'multi-scan '
_exptl_absorpt_correction_T_min   0.992
_exptl_absorpt_correction_T_max   0.995
_exptl_absorpt_process_details    'multi-scan '
_exptl_absorpt_special_details    '(SADABS; Sheldrick, 2003)'
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker Apex2 CCD'
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             8222
_diffrn_reflns_av_unetI/netI      0.0552
_diffrn_reflns_av_R_equivalents   0.0559
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        18
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          1.590
_diffrn_reflns_theta_max          27.189
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.893
_diffrn_measured_fraction_theta_full  0.985
_diffrn_reflns_Laue_measured_fraction_max    0.893
_diffrn_reflns_Laue_measured_fraction_full   0.985
_diffrn_reflns_point_group_measured_fraction_max   0.893
_diffrn_reflns_point_group_measured_fraction_full  0.985
_reflns_number_total              2760
_reflns_number_gt                 1660
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement         'SAINT (Bruker, 2005)'
_computing_data_reduction         'SAINT'
_computing_structure_solution     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL'
_computing_publication_material   'SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0999P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2463
_refine_ls_number_parameters      173
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0762
_refine_ls_R_factor_gt            0.0505
_refine_ls_wR_factor_ref          0.1652
_refine_ls_wR_factor_gt           0.1471
_refine_ls_goodness_of_fit_ref    0.987
_refine_ls_restrained_S_all       0.987
_refine_ls_shift/su_max           0.040
_refine_ls_shift/su_mean          0.001
 
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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.85474(5) 0.36446(15) 1.06147(4) 0.0490(3) Uani 1 1 d . . . . .
N2 N 0.66696(16) 0.2902(4) 1.00464(12) 0.0472(6) Uani 1 1 d . . . . .
C8 C 0.79405(19) 0.1288(5) 1.10238(14) 0.0431(6) Uani 1 1 d . . . . .
C9 C 0.69385(19) 0.1155(5) 1.06444(14) 0.0430(6) Uani 1 1 d . . . . .
C10 C 0.6305(2) -0.0656(6) 1.08730(16) 0.0535(7) Uani 1 1 d . . . . .
H10 H 0.5636 -0.0774 1.0625 0.064 Uiso 1 1 calc R U . . .
C1 C 0.74252(19) 0.4313(5) 0.99684(14) 0.0416(6) Uani 1 1 d . . . . .
C13 C 0.8328(2) -0.0321(6) 1.16326(15) 0.0514(7) Uani 1 1 d . . . . .
H13 H 0.8995 -0.0204 1.1889 0.062 Uiso 1 1 calc R U . . .
C12 C 0.7688(2) -0.2103(6) 1.18446(16) 0.0543(7) Uani 1 1 d . . . . .
H12 H 0.7932 -0.3225 1.2247 0.065 Uiso 1 1 calc R U . . .
C11 C 0.6696(2) -0.2255(6) 1.14726(15) 0.0533(7) Uani 1 1 d . . . . .
H11 H 0.6283 -0.3466 1.1632 0.064 Uiso 1 1 calc R U . . .
C2 C 0.73437(18) 0.6358(5) 0.93970(14) 0.0401(6) Uani 1 1 d . . . . .
C4 C 0.6344(2) 0.8962(6) 0.83782(14) 0.0487(7) Uani 1 1 d . . . . .
C3 C 0.64114(19) 0.6995(6) 0.89153(14) 0.0454(7) Uani 1 1 d . . . . .
C7 C 0.81683(19) 0.7779(5) 0.93103(14) 0.0448(7) Uani 1 1 d . . . . .
H7 H 0.8785 0.7392 0.9629 0.054 Uiso 1 1 calc R U . . .
C6 C 0.8121(2) 0.9735(6) 0.87766(15) 0.0479(7) Uani 1 1 d . . . . .
C5 C 0.7200(2) 1.0286(6) 0.83148(15) 0.0516(7) Uani 1 1 d . . . . .
H5 H 0.7148 1.1583 0.7948 0.062 Uiso 1 1 calc R U . . .
O1 O 0.55739(14) 0.5723(5) 0.89717(12) 0.0632(6) Uani 1 1 d . . . . .
H1A H 0.5766 0.4593 0.9322 0.076 Uiso 1 1 d R U . . .
O2 O 0.52433(19) 1.1281(6) 0.73945(14) 0.0911(9) Uani 1 1 d . . . . .
C15 C 0.9040(2) 1.1206(7) 0.8705(2) 0.0674(9) Uani 1 1 d . . . . .
H15A H 0.8860 1.2992 0.8471 0.101 Uiso 1 1 calc R U . . .
H15C H 0.9354 1.0051 0.8428 0.101 Uiso 1 1 calc R U . . .
H15B H 0.9492 1.1510 0.9170 0.101 Uiso 1 1 calc R U . . .
C14 C 0.5376(2) 0.9680(8) 0.78787(17) 0.0675(9) Uani 1 1 d . . . . .
H14 H 0.4819 0.8801 0.7949 0.081 Uiso 1 1 calc R U . . .
 
 
_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 C8 1.732(3) . ?
S1 C1 1.746(3) . ?
N2 C1 1.300(3) . ?
N2 C9 1.393(4) . ?
C8 C13 1.387(4) . ?
C8 C9 1.394(4) . ?
C9 C10 1.398(4) . ?
C10 C11 1.371(4) . ?
C1 C2 1.458(4) . ?
C13 C12 1.380(4) . ?
C12 C11 1.380(4) . ?
C2 C7 1.392(4) . ?
C2 C3 1.411(4) . ?
C4 C3 1.386(4) . ?
C4 C5 1.394(4) . ?
C4 C14 1.471(4) . ?
C3 O1 1.355(4) . ?
C7 C6 1.382(4) . ?
C6 C5 1.375(4) . ?
C6 C15 1.510(4) . ?
O2 C14 1.185(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 C1 89.33(15) . . ?
C1 N2 C9 111.6(2) . . ?
C13 C8 C9 121.5(3) . . ?
C13 C8 S1 128.7(2) . . ?
C9 C8 S1 109.8(2) . . ?
N2 C9 C8 114.3(2) . . ?
N2 C9 C10 126.0(2) . . ?
C8 C9 C10 119.8(3) . . ?
C11 C10 C9 118.4(3) . . ?
N2 C1 C2 122.9(2) . . ?
N2 C1 S1 115.0(2) . . ?
C2 C1 S1 122.2(2) . . ?
C12 C13 C8 117.6(3) . . ?
C11 C12 C13 121.4(3) . . ?
C10 C11 C12 121.3(3) . . ?
C7 C2 C3 117.6(3) . . ?
C7 C2 C1 121.9(2) . . ?
C3 C2 C1 120.6(2) . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 C14 120.6(3) . . ?
C5 C4 C14 119.8(3) . . ?
O1 C3 C4 119.1(2) . . ?
O1 C3 C2 120.9(3) . . ?
C4 C3 C2 119.9(3) . . ?
C6 C7 C2 123.6(2) . . ?
C5 C6 C7 117.2(3) . . ?
C5 C6 C15 121.5(3) . . ?
C7 C6 C15 121.4(3) . . ?
C6 C5 C4 122.1(3) . . ?
O2 C14 C4 125.6(3) . . ?
 
_refine_diff_density_max    0.351
_refine_diff_density_min   -0.272
_refine_diff_density_rms    0.061



