 
data_p1619d
 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C5 H11 N O2 S' 
_chemical_formula_sum
 'C5 H11 N O2 S' 
_chemical_formula_weight          149.21

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/c'
_space_group_name_Hall            '-P 2ybc'
 
_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, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    16.894(2)
_cell_length_b                    4.7953(6)
_cell_length_c                    9.8686(13)
_cell_angle_alpha                 90
_cell_angle_beta                  101.318(4)
_cell_angle_gamma                 90
_cell_volume                      783.94(18)
_cell_formula_units_Z             4
_cell_measurement_temperature     338(2)
_cell_measurement_reflns_used     8528
_cell_measurement_theta_min       3.69
_cell_measurement_theta_max       23.74
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.264          
_exptl_crystal_F_000              320
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.348
_exptl_crystal_size_mid           0.132
_exptl_crystal_size_min           0.064
_exptl_absorpt_coefficient_mu     0.347
_shelx_estimated_absorpt_T_min    0.889
_shelx_estimated_absorpt_T_max    0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7025
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_process_details 'SADABS 2014/5'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       338(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            'MoK\a'
_diffrn_source          	  'sealed tube'
_diffrn_radiation_monochromator   'graphite'
_diffrn_measurement_device        'Bruker D8 Quest Apex3'
_diffrn_radiation_detector	  'Photon100'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  10.4 
_diffrn_reflns_number             21783
_diffrn_reflns_av_unetI/netI      0.0077
_diffrn_reflns_av_R_equivalents   0.0243
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -5
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          2.459
_diffrn_reflns_theta_max          23.843
_diffrn_reflns_theta_full         23.843
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              1207
_reflns_number_gt                 1061
_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        'Apex3'
_computing_cell_refinement        'Peakref'
_computing_data_reduction         'SAINT,SADABS-2014/5'
_computing_structure_solution     'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics     'PLATON, Shelxle'
_computing_publication_material   ?
_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)+(0.1599P)²+0.4149P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          1207
_refine_ls_number_parameters      111
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0773
_refine_ls_R_factor_gt            0.0711
_refine_ls_wR_factor_ref          0.2368
_refine_ls_wR_factor_gt           0.2252
_refine_ls_goodness_of_fit_ref    1.055
_refine_ls_restrained_S_all       1.055
_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_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
N1 N 0.59176(16) 0.4429(5) 0.1443(2) 0.0477(7) Uani 1 1 d . . . . .
H1 H 0.607(2) 0.307(8) 0.092(4) 0.072 Uiso 1 1 d . U . . .
H2 H 0.598(2) 0.604(9) 0.108(4) 0.072 Uiso 1 1 d . U . . .
H3 H 0.533(2) 0.417(7) 0.155(4) 0.072 Uiso 1 1 d . U . . .
O1 O 0.56554(12) 0.8144(4) 0.33177(18) 0.0570(7) Uani 1 1 d . . . . .
O2 O 0.62384(16) 0.5507(4) 0.50788(19) 0.0697(8) Uani 1 1 d . . . . .
C1 C 0.60637(16) 0.6108(5) 0.3828(2) 0.0412(7) Uani 1 1 d . . . . .
C2 C 0.6460(6) 0.416(2) 0.2797(9) 0.0339(14) Uani 0.663(9) 1 d . . P A 1
H21 H 0.650925 0.221868 0.311031 0.041 Uiso 0.663(9) 1 calc R U P A 1
C3 C 0.7279(3) 0.5483(13) 0.2828(5) 0.0557(14) Uani 0.663(9) 1 d . . P A 1
H31 H 0.720375 0.739902 0.251386 0.067 Uiso 0.663(9) 1 calc R U P A 1
H32 H 0.757898 0.550882 0.377274 0.067 Uiso 0.663(9) 1 calc R U P A 1
C4 C 0.7761(4) 0.3972(18) 0.1945(9) 0.112(3) Uani 0.663(9) 1 d . . P A 1
H41 H 0.743901 0.382081 0.101879 0.134 Uiso 0.663(9) 1 calc R U P A 1
H42 H 0.786410 0.209548 0.230285 0.134 Uiso 0.663(9) 1 calc R U P A 1
S1 S 0.8693(2) 0.5546(11) 0.1841(5) 0.165(2) Uani 0.663(9) 1 d D . P A 1
C5 C 0.9254(13) 0.492(5) 0.324(2) 0.248(10) Uiso 0.663(9) 1 d D . P A 1
H51 H 0.977551 0.572917 0.325605 0.371 Uiso 0.663(9) 1 calc R U P A 1
H52 H 0.902707 0.571263 0.397668 0.371 Uiso 0.663(9) 1 calc R U P A 1
H53 H 0.930766 0.294303 0.337061 0.371 Uiso 0.663(9) 1 calc R U P A 1
C2B C 0.6334(13) 0.452(5) 0.301(2) 0.0339(14) Uani 0.337(9) 1 d . . P A 2
H22B H 0.617217 0.269751 0.331682 0.041 Uiso 0.337(9) 1 calc R U P A 2
C3B C 0.7265(10) 0.391(5) 0.2962(18) 0.108(6) Uiso 0.337(9) 1 d . . P A 2
H33B H 0.752751 0.303096 0.381748 0.130 Uiso 0.337(9) 1 calc R U P A 2
H34B H 0.729584 0.264351 0.220793 0.130 Uiso 0.337(9) 1 calc R U P A 2
C4B C 0.7664(16) 0.639(6) 0.278(3) 0.167(10) Uiso 0.337(9) 1 d . . P A 2
H43B H 0.757456 0.775722 0.345718 0.200 Uiso 0.337(9) 1 calc R U P A 2
H44B H 0.745580 0.714190 0.186446 0.200 Uiso 0.337(9) 1 calc R U P A 2
S1B S 0.8804(6) 0.562(5) 0.299(3) 0.382(15) Uani 0.337(9) 1 d D . P A 2
C5B C 0.888(3) 0.285(9) 0.378(6) 0.39(4) Uiso 0.337(9) 1 d D . P A 2
H54B H 0.942829 0.223695 0.395409 0.578 Uiso 0.337(9) 1 calc R U P A 2
H55B H 0.870659 0.311411 0.464657 0.578 Uiso 0.337(9) 1 calc R U P A 2
H56B H 0.854122 0.147500 0.324488 0.578 Uiso 0.337(9) 1 calc R U P A 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
N1 C2 1.469(10) . ?
N1 C2B 1.57(2) . ?
N1 H1 0.91(4) . ?
N1 H2 0.87(4) . ?
N1 H3 1.03(4) . ?
O1 C1 1.243(3) . ?
O2 C1 1.246(3) . ?
C1 C2B 1.260(16) . ?
C1 C2 1.619(6) . ?
C2 C3 1.518(11) . ?
C2 H21 0.9800 . ?
C3 C4 1.491(8) . ?
C3 H31 0.9700 . ?
C3 H32 0.9700 . ?
C4 S1 1.768(7) . ?
C4 H41 0.9700 . ?
C4 H42 0.9700 . ?
S1 C5 1.55(2) . ?
C5 H51 0.9600 . ?
C5 H52 0.9600 . ?
C5 H53 0.9600 . ?
C2B C3B 1.61(2) . ?
C2B H22B 0.9800 . ?
C3B C4B 1.40(3) . ?
C3B H33B 0.9700 . ?
C3B H34B 0.9700 . ?
C4B S1B 1.93(3) . ?
C4B H43B 0.9700 . ?
C4B H44B 0.9700 . ?
S1B C5B 1.54(3) . ?
C5B H54B 0.9600 . ?
C5B H55B 0.9600 . ?
C5B H56B 0.9600 . ?
 
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 N1 H1 105(2) . . ?
C2B N1 H1 118(2) . . ?
C2 N1 H2 111(2) . . ?
C2B N1 H2 109(2) . . ?
H1 N1 H2 109(3) . . ?
C2 N1 H3 109.7(19) . . ?
C2B N1 H3 99(2) . . ?
H1 N1 H3 112(3) . . ?
H2 N1 H3 110(3) . . ?
C2B C1 O1 117.3(11) . . ?
C2B C1 O2 116.7(11) . . ?
O1 C1 O2 126.0(2) . . ?
O1 C1 C2 117.6(4) . . ?
O2 C1 C2 116.3(4) . . ?
N1 C2 C3 112.7(6) . . ?
N1 C2 C1 105.1(5) . . ?
C3 C2 C1 103.6(6) . . ?
N1 C2 H21 111.7 . . ?
C3 C2 H21 111.7 . . ?
C1 C2 H21 111.7 . . ?
C4 C3 C2 112.7(5) . . ?
C4 C3 H31 109.1 . . ?
C2 C3 H31 109.1 . . ?
C4 C3 H32 109.1 . . ?
C2 C3 H32 109.1 . . ?
H31 C3 H32 107.8 . . ?
C3 C4 S1 114.9(5) . . ?
C3 C4 H41 108.5 . . ?
S1 C4 H41 108.5 . . ?
C3 C4 H42 108.5 . . ?
S1 C4 H42 108.5 . . ?
H41 C4 H42 107.5 . . ?
C5 S1 C4 105.2(9) . . ?
S1 C5 H51 109.5 . . ?
S1 C5 H52 109.5 . . ?
H51 C5 H52 109.5 . . ?
S1 C5 H53 109.5 . . ?
H51 C5 H53 109.5 . . ?
H52 C5 H53 109.5 . . ?
C1 C2B N1 119.9(15) . . ?
C1 C2B C3B 127.4(19) . . ?
N1 C2B C3B 102.6(11) . . ?
C1 C2B H22B 100.5 . . ?
N1 C2B H22B 100.5 . . ?
C3B C2B H22B 100.5 . . ?
C4B C3B C2B 110(2) . . ?
C4B C3B H33B 109.6 . . ?
C2B C3B H33B 109.6 . . ?
C4B C3B H34B 109.6 . . ?
C2B C3B H34B 109.6 . . ?
H33B C3B H34B 108.1 . . ?
C3B C4B S1B 108.6(19) . . ?
C3B C4B H43B 110.0 . . ?
S1B C4B H43B 110.0 . . ?
C3B C4B H44B 110.0 . . ?
S1B C4B H44B 110.0 . . ?
H43B C4B H44B 108.3 . . ?
C4B S1B C5B 101(2) . . ?
S1B C5B H54B 109.5 . . ?
S1B C5B H55B 109.5 . . ?
H54B C5B H55B 109.5 . . ?
S1B C5B H56B 109.5 . . ?
H54B C5B H56B 109.5 . . ?
H55B C5B H56B 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O1 C1 C2 N1 -28.2(7) . . . . ?
O2 C1 C2 N1 155.9(4) . . . . ?
O1 C1 C2 C3 90.2(6) . . . . ?
O2 C1 C2 C3 -85.7(6) . . . . ?
N1 C2 C3 C4 -67.7(8) . . . . ?
C1 C2 C3 C4 179.3(6) . . . . ?
C2 C3 C4 S1 175.8(6) . . . . ?
C3 C4 S1 C5 74.7(12) . . . . ?
O1 C1 C2B N1 -22(2) . . . . ?
O2 C1 C2B N1 158.4(12) . . . . ?
O1 C1 C2B C3B 117(2) . . . . ?
O2 C1 C2B C3B -62(2) . . . . ?
C1 C2B C3B C4B -57(3) . . . . ?
N1 C2B C3B C4B 87(2) . . . . ?
C2B C3B C4B S1B 172.1(17) . . . . ?
 
_refine_diff_density_max    0.417
_refine_diff_density_min   -0.350
_refine_diff_density_rms    0.060



