#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024476.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_4024476
loop_
_publ_author_name
'Michael Harmata'
'Kanok-on Rayanil'
'Vinson R. Espejo'
'Charles L. Barnes'
_publ_section_title
;
Benzothiazines in Synthesis. Further Studies of the Intramolecular,
Stereoselective Addition of Sulfonimidoyl Carbanions to α,β-Unsaturated
Functional Groups
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3214
_journal_page_last               3216
_journal_paper_doi               10.1021/jo900151d
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C21 H19 N O3 S2'
_chemical_formula_weight         397.49
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9218(5)
_cell_length_b                   12.0276(7)
_cell_length_c                   17.7965(10)
_cell_measurement_reflns_used    8819
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.3
_cell_volume                     1909.70(19)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13078
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         2.04
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0327P)²+0.3990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0713
_reflns_number_gt                3877
_reflns_number_total             4179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900151d_si_005.cif
_cod_data_source_block           KR-VIII-86a1
_cod_database_code               4024476
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.30751(5) 0.81034(4) 0.03408(2) 0.02277(10) Uani 1 1 d . . .
O1 O 1.44075(15) 0.82932(12) 0.07946(7) 0.0314(3) Uani 1 1 d . . .
N1 N 1.30262(19) 0.71489(12) -0.02293(8) 0.0268(3) Uani 1 1 d . . .
C1 C 1.1539(2) 0.79143(15) 0.09530(9) 0.0249(4) Uani 1 1 d . . .
H1A H 1.1535 0.8505 0.1341 0.030 Uiso 1 1 calc R . .
H1B H 1.0589 0.7960 0.0668 0.030 Uiso 1 1 calc R . .
S2 S 0.97972(5) 0.72292(4) 0.25354(2) 0.02787(11) Uani 1 1 d . . .
O2 O 0.99425(17) 0.84045(11) 0.24086(8) 0.0394(4) Uani 1 1 d . . .
C2 C 1.1676(2) 0.67650(15) 0.13292(9) 0.0236(4) Uani 1 1 d . . .
H2 H 1.2434 0.6818 0.1741 0.028 Uiso 1 1 calc R . .
O3 O 1.06966(17) 0.67285(14) 0.31164(7) 0.0407(4) Uani 1 1 d . . .
C3 C 1.2166(2) 0.58399(15) 0.07866(10) 0.0236(4) Uani 1 1 d . . .
C4 C 1.2085(2) 0.47301(16) 0.10130(10) 0.0307(4) Uani 1 1 d . . .
H4 H 1.1760 0.4565 0.1509 0.037 Uiso 1 1 calc R . .
C5 C 1.2463(3) 0.38631(17) 0.05398(12) 0.0372(5) Uani 1 1 d . . .
H5 H 1.2397 0.3116 0.0709 0.045 Uiso 1 1 calc R . .
C6 C 1.2942(3) 0.40970(16) -0.01904(12) 0.0369(5) Uani 1 1 d . . .
H6 H 1.3172 0.3508 -0.0527 0.044 Uiso 1 1 calc R . .
C7 C 1.3080(2) 0.51866(16) -0.04199(11) 0.0315(4) Uani 1 1 d . . .
H7 H 1.3415 0.5340 -0.0916 0.038 Uiso 1 1 calc R . .
C8 C 1.2740(2) 0.60691(14) 0.00594(10) 0.0236(4) Uani 1 1 d . . .
C9 C 1.2704(2) 0.92926(15) -0.02041(9) 0.0234(4) Uani 1 1 d . . .
C10 C 1.3674(2) 1.01867(15) -0.01498(10) 0.0285(4) Uani 1 1 d . . .
H10 H 1.4492 1.0174 0.0192 0.034 Uiso 1 1 calc R . .
C11 C 1.3421(3) 1.11014(17) -0.06056(13) 0.0368(5) Uani 1 1 d . . .
H11 H 1.4083 1.1719 -0.0584 0.044 Uiso 1 1 calc R . .
C12 C 1.2213(3) 1.11222(18) -0.10917(13) 0.0413(5) Uani 1 1 d . . .
H12 H 1.2043 1.1758 -0.1397 0.050 Uiso 1 1 calc R . .
C13 C 1.1247(3) 1.02180(19) -0.11369(12) 0.0381(5) Uani 1 1 d . . .
H13 H 1.0413 1.0240 -0.1469 0.046 Uiso 1 1 calc R . .
C14 C 1.1497(2) 0.92848(17) -0.06984(11) 0.0296(4) Uani 1 1 d . . .
H14 H 1.0860 0.8654 -0.0735 0.035 Uiso 1 1 calc R . .
C15 C 1.0139(2) 0.64944(16) 0.16836(9) 0.0257(4) Uani 1 1 d . . .
H15A H 1.0085 0.5686 0.1785 0.031 Uiso 1 1 calc R . .
H15B H 0.9340 0.6679 0.1318 0.031 Uiso 1 1 calc R . .
C16 C 0.7882(2) 0.69259(16) 0.27005(9) 0.0268(4) Uani 1 1 d . . .
C17 C 0.6798(2) 0.76319(17) 0.24032(10) 0.0335(4) Uani 1 1 d . . .
H17 H 0.7076 0.8275 0.2126 0.040 Uiso 1 1 calc R . .
C18 C 0.5305(2) 0.73748(18) 0.25206(12) 0.0395(5) Uani 1 1 d . . .
H18 H 0.4550 0.7857 0.2332 0.047 Uiso 1 1 calc R . .
C19 C 0.4898(3) 0.64301(19) 0.29070(11) 0.0388(5) Uani 1 1 d . . .
H19 H 0.3868 0.6260 0.2979 0.047 Uiso 1 1 calc R . .
C20 C 0.5989(3) 0.5730(2) 0.31895(12) 0.0392(5) Uani 1 1 d . . .
H20 H 0.5706 0.5077 0.3455 0.047 Uiso 1 1 calc R . .
C21 C 0.7495(3) 0.59749(18) 0.30879(11) 0.0348(5) Uani 1 1 d . . .
H21 H 0.8247 0.5495 0.3282 0.042 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 120.54(9) . . ?
O1 S1 C9 109.38(9) . . ?
N1 S1 C9 103.81(8) . . ?
O1 S1 C1 108.16(8) . . ?
N1 S1 C1 106.86(9) . . ?
C9 S1 C1 107.40(9) . . ?
C8 N1 S1 116.79(11) . . ?
C2 C1 S1 108.82(12) . . ?
C2 C1 H1A 109.9 . . ?
S1 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
S1 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
O2 S2 O3 118.27(10) . . ?
O2 S2 C16 108.39(9) . . ?
O3 S2 C16 109.40(9) . . ?
O2 S2 C15 109.81(9) . . ?
O3 S2 C15 107.94(9) . . ?
C16 S2 C15 101.77(9) . . ?
C3 C2 C1 113.51(14) . . ?
C3 C2 C15 110.90(15) . . ?
C1 C2 C15 107.25(15) . . ?
C3 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C15 C2 H2 108.3 . . ?
C4 C3 C8 117.88(16) . . ?
C4 C3 C2 119.74(15) . . ?
C8 C3 C2 122.36(16) . . ?
C5 C4 C3 122.20(17) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 119.31(18) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 119.64(18) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 121.52(18) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C3 119.23(16) . . ?
C7 C8 N1 115.82(15) . . ?
C3 C8 N1 124.94(15) . . ?
C10 C9 C14 122.24(17) . . ?
C10 C9 S1 118.43(14) . . ?
C14 C9 S1 119.25(14) . . ?
C9 C10 C11 118.35(19) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.38(19) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 118.41(19) . . ?
C13 C14 H14 120.8 . . ?
C9 C14 H14 120.8 . . ?
C2 C15 S2 113.27(13) . . ?
C2 C15 H15A 108.9 . . ?
S2 C15 H15A 108.9 . . ?
C2 C15 H15B 108.9 . . ?
S2 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C21 C16 C17 121.47(19) . . ?
C21 C16 S2 119.67(16) . . ?
C17 C16 S2 118.79(15) . . ?
C18 C17 C16 118.38(18) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 118.9(2) . . ?
C16 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
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 O1 1.4552(14) . ?
S1 N1 1.5327(14) . ?
S1 C9 1.7594(18) . ?
S1 C1 1.7653(18) . ?
N1 C8 1.420(2) . ?
C1 C2 1.541(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
S2 O2 1.4374(15) . ?
S2 O3 1.4407(15) . ?
S2 C16 1.7720(19) . ?
S2 C15 1.7811(17) . ?
C2 C3 1.537(2) . ?
C2 C15 1.544(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.396(3) . ?
C3 C8 1.419(2) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(2) . ?
C7 H7 0.9500 . ?
C9 C10 1.383(3) . ?
C9 C14 1.391(3) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.380(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
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 S1 N1 C8 79.55(16) . . . . ?
C9 S1 N1 C8 -157.64(14) . . . . ?
C1 S1 N1 C8 -44.30(17) . . . . ?
O1 S1 C1 C2 -72.83(13) . . . . ?
N1 S1 C1 C2 58.33(13) . . . . ?
C9 S1 C1 C2 169.21(12) . . . . ?
S1 C1 C2 C3 -42.08(17) . . . . ?
S1 C1 C2 C15 -164.94(12) . . . . ?
C1 C2 C3 C4 -168.86(17) . . . . ?
C15 C2 C3 C4 -48.0(2) . . . . ?
C1 C2 C3 C8 12.7(2) . . . . ?
C15 C2 C3 C8 133.49(18) . . . . ?
C8 C3 C4 C5 -3.7(3) . . . . ?
C2 C3 C4 C5 177.75(19) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 2.2(3) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C3 -3.3(3) . . . . ?
C6 C7 C8 N1 175.9(2) . . . . ?
C4 C3 C8 C7 5.3(3) . . . . ?
C2 C3 C8 C7 -176.24(18) . . . . ?
C4 C3 C8 N1 -173.85(18) . . . . ?
C2 C3 C8 N1 4.6(3) . . . . ?
S1 N1 C8 C7 -163.91(15) . . . . ?
S1 N1 C8 C3 15.2(3) . . . . ?
O1 S1 C9 C10 1.29(17) . . . . ?
N1 S1 C9 C10 -128.59(15) . . . . ?
C1 S1 C9 C10 118.46(15) . . . . ?
O1 S1 C9 C14 178.28(14) . . . . ?
N1 S1 C9 C14 48.40(17) . . . . ?
C1 S1 C9 C14 -64.56(16) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
S1 C9 C10 C11 176.96(15) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C9 1.7(3) . . . . ?
C10 C9 C14 C13 -1.5(3) . . . . ?
S1 C9 C14 C13 -178.33(16) . . . . ?
C3 C2 C15 S2 159.12(12) . . . . ?
C1 C2 C15 S2 -76.42(15) . . . . ?
O2 S2 C15 C2 55.83(16) . . . . ?
O3 S2 C15 C2 -74.39(15) . . . . ?
C16 S2 C15 C2 170.51(13) . . . . ?
O2 S2 C16 C21 -157.25(15) . . . . ?
O3 S2 C16 C21 -26.99(17) . . . . ?
C15 S2 C16 C21 87.02(16) . . . . ?
O2 S2 C16 C17 25.73(16) . . . . ?
O3 S2 C16 C17 155.99(15) . . . . ?
C15 S2 C16 C17 -89.99(16) . . . . ?
C21 C16 C17 C18 1.6(3) . . . . ?
S2 C16 C17 C18 178.57(15) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C17 C16 C21 C20 -0.8(3) . . . . ?
S2 C16 C21 C20 -177.78(16) . . . . ?
C19 C20 C21 C16 -0.1(3) . . . . ?
