#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/64/1506487.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_1506487
loop_
_publ_author_name
'Harmata, Michael'
'Rayanil, Kanok-On'
'Gomes, Maria G.'
'Zheng, Pinguan'
'Calkins, Nathan L.'
'Kim, Soo-Yeun'
'Fan, Yimin'
'Bumbu, Valentina'
'Lee, Dong Reyoul'
'Wacharasindhu, Sumrit'
'Hong, Xuechuan'
_publ_section_title
;
 New synthesis of benzothiazines and benzoisothiazoles containing a
 sulfoximine functional group.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              143
_journal_page_last               145
_journal_paper_doi               10.1021/ol047781j
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C8 H7 N O2 S'
_chemical_formula_weight         181.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.1290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2041(7)
_cell_length_b                   8.0433(7)
_cell_length_c                   12.2666(10)
_cell_measurement_reflns_used    2880
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.5
_cell_volume                     791.38(12)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5489
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0446P)²+0.4153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1507
_reflns_number_total             1753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol047781jsi20041028_100238.cif
_cod_data_source_block           MG-III-016c
_cod_original_sg_symbol_H-M      P2~1~/c
_cod_database_code               1506487
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1 S 0.29704(5) 0.19570(5) 0.55984(4) 0.02743(15) Uani 1 1 d .
O1 O 0.17476(17) 0.06476(17) 0.54458(13) 0.0447(4) Uani 1 1 d .
N1 N 0.34607(19) 0.2664(2) 0.45117(12) 0.0312(4) Uani 1 1 d .
C1 C 0.3090(2) 0.4339(2) 0.43882(13) 0.0268(4) Uani 1 1 d .
O2 O 0.32947(17) 0.51664(18) 0.35967(10) 0.0385(3) Uani 1 1 d .
C2 C 0.24050(19) 0.5028(2) 0.53430(13) 0.0227(3) Uani 1 1 d .
C3 C 0.1907(2) 0.6632(2) 0.55056(14) 0.0275(4) Uani 1 1 d .
H3 H 0.1977 0.7484 0.4982 0.033 Uiso 1 1 calc R
C4 C 0.1297(2) 0.6962(2) 0.64607(16) 0.0314(4) Uani 1 1 d .
H4 H 0.0952 0.8059 0.6591 0.038 Uiso 1 1 calc R
C5 C 0.1184(2) 0.5718(2) 0.72270(15) 0.0313(4) Uani 1 1 d .
H5 H 0.0751 0.5975 0.7867 0.038 Uiso 1 1 calc R
C6 C 0.1693(2) 0.4106(2) 0.70717(14) 0.0281(4) Uani 1 1 d .
H6 H 0.1628 0.3248 0.7593 0.034 Uiso 1 1 calc R
C7 C 0.22973(19) 0.3813(2) 0.61234(13) 0.0230(3) Uani 1 1 d .
C8 C 0.4785(2) 0.1288(2) 0.65153(16) 0.0340(4) Uani 1 1 d .
H8A H 0.4523 0.1003 0.7236 0.051 Uiso 1 1 calc R
H8B H 0.5617 0.2180 0.6619 0.051 Uiso 1 1 calc R
H8C H 0.5231 0.0307 0.6204 0.051 Uiso 1 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 0.0277(2) 0.0201(2) 0.0331(3) -0.00067(17) 0.00320(17) -0.00010(16)
O1 0.0394(8) 0.0240(7) 0.0658(10) 0.0009(6) -0.0005(7) -0.0079(6)
N1 0.0369(8) 0.0310(8) 0.0253(7) -0.0051(6) 0.0057(6) 0.0042(7)
C1 0.0258(8) 0.0301(9) 0.0239(8) -0.0007(7) 0.0040(6) -0.0022(7)
O2 0.0478(8) 0.0437(8) 0.0273(6) 0.0054(6) 0.0155(6) 0.0015(6)
C2 0.0216(7) 0.0231(8) 0.0232(8) -0.0004(6) 0.0039(6) -0.0033(6)
C3 0.0284(8) 0.0236(9) 0.0303(9) 0.0034(7) 0.0060(7) -0.0005(7)
C4 0.0293(8) 0.0271(9) 0.0381(10) -0.0059(8) 0.0076(7) 0.0023(7)
C5 0.0280(8) 0.0404(10) 0.0273(8) -0.0041(8) 0.0100(7) 0.0012(8)
C6 0.0244(8) 0.0339(9) 0.0263(8) 0.0065(7) 0.0059(7) -0.0017(7)
C7 0.0204(7) 0.0214(8) 0.0268(8) 0.0012(6) 0.0039(6) -0.0006(6)
C8 0.0306(9) 0.0358(10) 0.0349(10) 0.0056(8) 0.0053(8) 0.0085(8)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 N1 116.65(9)
O1 S1 C8 109.51(9)
N1 S1 C8 108.67(9)
O1 S1 C7 113.87(8)
N1 S1 C7 99.13(8)
C8 S1 C7 108.38(9)
C1 N1 S1 110.78(12)
O2 C1 N1 123.80(16)
O2 C1 C2 123.71(16)
N1 C1 C2 112.49(14)
C3 C2 C7 119.73(15)
C3 C2 C1 128.76(15)
C7 C2 C1 111.51(15)
C2 C3 C4 118.01(16)
C5 C4 C3 121.23(16)
C6 C5 C4 121.02(16)
C7 C6 C5 116.61(16)
C6 C7 C2 123.40(16)
C6 C7 S1 130.57(14)
C2 C7 S1 105.97(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4393(14)
S1 N1 1.5772(16)
S1 C8 1.7514(18)
S1 C7 1.7603(17)
N1 C1 1.382(2)
C1 O2 1.218(2)
C1 C2 1.507(2)
C2 C3 1.381(2)
C2 C7 1.383(2)
C3 C4 1.393(2)
C4 C5 1.390(3)
C5 C6 1.387(3)
C6 C7 1.377(2)
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
O1 S1 N1 C1 119.26(13)
C8 S1 N1 C1 -116.40(13)
C7 S1 N1 C1 -3.36(13)
S1 N1 C1 O2 -177.36(14)
S1 N1 C1 C2 2.65(18)
O2 C1 C2 C3 -0.2(3)
N1 C1 C2 C3 179.81(16)
O2 C1 C2 C7 179.70(16)
N1 C1 C2 C7 -0.3(2)
C7 C2 C3 C4 -0.4(2)
C1 C2 C3 C4 179.48(15)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 C6 0.7(3)
C4 C5 C6 C7 -0.4(3)
C5 C6 C7 C2 -0.3(2)
C5 C6 C7 S1 -176.88(13)
C3 C2 C7 C6 0.7(2)
C1 C2 C7 C6 -179.19(14)
C3 C2 C7 S1 178.02(13)
C1 C2 C7 S1 -1.87(16)
O1 S1 C7 C6 55.55(18)
N1 S1 C7 C6 -179.85(16)
C8 S1 C7 C6 -66.57(17)
O1 S1 C7 C2 -121.51(12)
N1 S1 C7 C2 3.10(13)
C8 S1 C7 C2 116.37(12)
