#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024474.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_4024474
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_absolute_configuration rmad
_chemical_formula_sum            'C22 H18 Cl N O2 S'
_chemical_formula_weight         395.88
_space_group_IT_number           76
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      76
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_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                   14.1895(4)
_cell_length_b                   14.1895(4)
_cell_length_c                   9.7550(6)
_cell_measurement_reflns_used    7104
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.5
_cell_volume                     1964.09(14)
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13960
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         1.44
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.71
_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    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4257
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0361
_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)+(0.0469P)²+0.2846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                3777
_reflns_number_total             4257
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900151d_si_003.cif
_cod_data_source_block           VE-1-118
_cod_database_code               4024474
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z+1/4'
'-x, -y, z+1/2'
'y, -x, z+3/4'
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
Cl1 Cl 1.23312(7) 0.14642(6) 0.82296(8) 0.0860(3) Uani 1 1 d . . .
S1 S 0.66236(3) 0.65840(4) 0.87292(6) 0.03253(13) Uani 1 1 d . . .
O1 O 0.61570(12) 0.61344(13) 0.98799(17) 0.0512(5) Uani 1 1 d . . .
O2 O 0.94692(10) 0.47644(10) 1.07316(15) 0.0354(3) Uani 1 1 d . . .
N1 N 0.71817(14) 0.74914(14) 0.8947(3) 0.0512(6) Uani 1 1 d . . .
C1 C 0.73881(13) 0.57409(13) 0.7972(2) 0.0266(4) Uani 1 1 d . . .
H1A H 0.7074 0.5120 0.7908 0.032 Uiso 1 1 calc R . .
H1B H 0.7575 0.5943 0.7040 0.032 Uiso 1 1 calc R . .
C2 C 0.82549(13) 0.56841(13) 0.8917(2) 0.0257(4) Uani 1 1 d . . .
H2 H 0.8026 0.5536 0.9863 0.031 Uiso 1 1 calc R . .
C3 C 0.87330(14) 0.66460(13) 0.89653(19) 0.0261(4) Uani 1 1 d . . .
C4 C 0.97088(14) 0.67448(15) 0.8993(2) 0.0306(4) Uani 1 1 d . . .
H4 H 1.0093 0.6196 0.8969 0.037 Uiso 1 1 calc R . .
C5 C 1.01335(17) 0.76196(16) 0.9055(2) 0.0408(5) Uani 1 1 d . . .
H5 H 1.0801 0.7668 0.9056 0.049 Uiso 1 1 calc R . .
C6 C 0.95853(18) 0.84239(16) 0.9115(2) 0.0436(6) Uani 1 1 d . . .
H6 H 0.9875 0.9026 0.9174 0.052 Uiso 1 1 calc R . .
C7 C 0.86217(18) 0.83478(16) 0.9090(2) 0.0426(6) Uani 1 1 d . . .
H7 H 0.8248 0.8903 0.9130 0.051 Uiso 1 1 calc R . .
C8 C 0.81783(15) 0.74719(14) 0.9006(2) 0.0333(5) Uani 1 1 d . . .
C9 C 0.57535(14) 0.68461(14) 0.7495(2) 0.0289(4) Uani 1 1 d . . .
C10 C 0.50200(14) 0.62138(16) 0.7328(2) 0.0342(5) Uani 1 1 d . . .
H10 H 0.4975 0.5670 0.7893 0.041 Uiso 1 1 calc R . .
C11 C 0.43503(15) 0.63863(18) 0.6322(3) 0.0428(5) Uani 1 1 d . . .
H11 H 0.3846 0.5955 0.6190 0.051 Uiso 1 1 calc R . .
C12 C 0.44140(16) 0.71770(18) 0.5516(3) 0.0442(6) Uani 1 1 d . . .
H12 H 0.3949 0.7292 0.4835 0.053 Uiso 1 1 calc R . .
C13 C 0.51453(18) 0.78066(18) 0.5686(3) 0.0473(6) Uani 1 1 d . . .
H13 H 0.5182 0.8351 0.5122 0.057 Uiso 1 1 calc R . .
C14 C 0.58280(16) 0.76457(15) 0.6680(3) 0.0389(5) Uani 1 1 d . . .
H14 H 0.6336 0.8074 0.6800 0.047 Uiso 1 1 calc R . .
C15 C 0.88786(13) 0.48596(13) 0.8442(2) 0.0265(4) Uani 1 1 d . . .
H15A H 0.8468 0.4346 0.8103 0.032 Uiso 1 1 calc R . .
H15B H 0.9273 0.5074 0.7666 0.032 Uiso 1 1 calc R . .
C16 C 0.95162(13) 0.44707(13) 0.9557(2) 0.0258(4) Uani 1 1 d . . .
C17 C 1.01908(13) 0.37073(13) 0.91851(19) 0.0244(4) Uani 1 1 d . . .
C18 C 1.02867(15) 0.33659(14) 0.7856(2) 0.0307(4) Uani 1 1 d . . .
H18 H 0.9903 0.3613 0.7144 0.037 Uiso 1 1 calc R . .
C19 C 1.09377(17) 0.26679(15) 0.7564(2) 0.0397(5) Uani 1 1 d . . .
H19 H 1.1001 0.2432 0.6657 0.048 Uiso 1 1 calc R . .
C20 C 1.14943(17) 0.23182(16) 0.8609(3) 0.0442(6) Uani 1 1 d . . .
C21 C 1.14004(17) 0.26339(17) 0.9942(3) 0.0441(6) Uani 1 1 d . . .
H21 H 1.1783 0.2380 1.0651 0.053 Uiso 1 1 calc R . .
C22 C 1.07458(15) 0.33191(15) 1.0229(2) 0.0339(5) Uani 1 1 d . . .
H22 H 1.0669 0.3532 1.1146 0.041 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'
Cl Cl 0.1484 0.1585 '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 120.00(13) . . ?
O1 S1 C9 107.53(10) . . ?
N1 S1 C9 106.27(11) . . ?
O1 S1 C1 107.72(10) . . ?
N1 S1 C1 108.01(10) . . ?
C9 S1 C1 106.61(9) . . ?
C8 N1 S1 120.49(15) . . ?
C2 C1 S1 105.91(13) . . ?
C2 C1 H1A 110.6 . . ?
S1 C1 H1A 110.6 . . ?
C2 C1 H1B 110.6 . . ?
S1 C1 H1B 110.6 . . ?
H1A C1 H1B 108.7 . . ?
C3 C2 C15 115.72(16) . . ?
C3 C2 C1 109.08(15) . . ?
C15 C2 C1 108.60(15) . . ?
C3 C2 H2 107.7 . . ?
C15 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C4 C3 C8 118.06(18) . . ?
C4 C3 C2 122.22(17) . . ?
C8 C3 C2 119.71(17) . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 121.4(2) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C3 119.3(2) . . ?
C7 C8 N1 115.8(2) . . ?
C3 C8 N1 124.88(18) . . ?
C10 C9 C14 121.27(19) . . ?
C10 C9 S1 118.05(16) . . ?
C14 C9 S1 120.63(16) . . ?
C9 C10 C11 118.9(2) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 118.7(2) . . ?
C13 C14 H14 120.6 . . ?
C9 C14 H14 120.6 . . ?
C16 C15 C2 113.79(16) . . ?
C16 C15 H15A 108.8 . . ?
C2 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C2 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 C17 120.77(17) . . ?
O2 C16 C15 121.02(17) . . ?
C17 C16 C15 118.20(16) . . ?
C18 C17 C22 119.07(18) . . ?
C18 C17 C16 122.89(17) . . ?
C22 C17 C16 118.04(17) . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.1(2) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 121.50(19) . . ?
C19 C20 Cl1 118.98(19) . . ?
C21 C20 Cl1 119.51(18) . . ?
C22 C21 C20 119.1(2) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C17 120.7(2) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
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
Cl1 C20 1.736(2) . ?
S1 O1 1.4510(18) . ?
S1 N1 1.526(2) . ?
S1 C9 1.764(2) . ?
S1 C1 1.7760(19) . ?
O2 C16 1.221(2) . ?
N1 C8 1.416(3) . ?
C1 C2 1.539(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.525(3) . ?
C2 C15 1.538(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.392(3) . ?
C3 C8 1.412(3) . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.384(3) . ?
C9 C14 1.390(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.518(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.490(3) . ?
C17 C18 1.391(3) . ?
C17 C22 1.400(3) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(4) . ?
C21 C22 1.373(3) . ?
C21 H21 0.9500 . ?
C22 H22 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 102.5(2) . . . . ?
C9 S1 N1 C8 -135.4(2) . . . . ?
C1 S1 N1 C8 -21.3(3) . . . . ?
O1 S1 C1 C2 -77.04(15) . . . . ?
N1 S1 C1 C2 53.94(17) . . . . ?
C9 S1 C1 C2 167.79(13) . . . . ?
S1 C1 C2 C3 -61.51(17) . . . . ?
S1 C1 C2 C15 171.56(14) . . . . ?
C15 C2 C3 C4 -18.9(3) . . . . ?
C1 C2 C3 C4 -141.62(19) . . . . ?
C15 C2 C3 C8 162.19(18) . . . . ?
C1 C2 C3 C8 39.4(2) . . . . ?
C8 C3 C4 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 -179.11(19) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C6 C7 C8 C3 0.9(3) . . . . ?
C6 C7 C8 N1 -178.2(2) . . . . ?
C4 C3 C8 C7 -0.8(3) . . . . ?
C2 C3 C8 C7 178.15(19) . . . . ?
C4 C3 C8 N1 178.1(2) . . . . ?
C2 C3 C8 N1 -2.9(3) . . . . ?
S1 N1 C8 C7 174.70(19) . . . . ?
S1 N1 C8 C3 -4.3(4) . . . . ?
O1 S1 C9 C10 -36.25(18) . . . . ?
N1 S1 C9 C10 -165.92(17) . . . . ?
C1 S1 C9 C10 79.05(17) . . . . ?
O1 S1 C9 C14 146.35(18) . . . . ?
N1 S1 C9 C14 16.7(2) . . . . ?
C1 S1 C9 C14 -98.35(18) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
S1 C9 C10 C11 -177.24(17) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C9 -0.4(4) . . . . ?
C10 C9 C14 C13 0.3(3) . . . . ?
S1 C9 C14 C13 177.62(18) . . . . ?
C3 C2 C15 C16 80.5(2) . . . . ?
C1 C2 C15 C16 -156.53(16) . . . . ?
C2 C15 C16 O2 4.6(3) . . . . ?
C2 C15 C16 C17 -176.48(16) . . . . ?
O2 C16 C17 C18 -178.4(2) . . . . ?
C15 C16 C17 C18 2.7(3) . . . . ?
O2 C16 C17 C22 1.9(3) . . . . ?
C15 C16 C17 C22 -177.00(18) . . . . ?
C22 C17 C18 C19 -1.5(3) . . . . ?
C16 C17 C18 C19 178.76(19) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 1.5(4) . . . . ?
C18 C19 C20 Cl1 -178.35(18) . . . . ?
C19 C20 C21 C22 -0.8(4) . . . . ?
Cl1 C20 C21 C22 179.08(19) . . . . ?
C20 C21 C22 C17 -1.1(4) . . . . ?
C18 C17 C22 C21 2.3(3) . . . . ?
C16 C17 C22 C21 -178.0(2) . . . . ?
