#------------------------------------------------------------------------------
#$Date: 2017-08-05 15:43:53 +0300 (Sat, 05 Aug 2017) $
#$Revision: 199561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/67/1546762.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_1546762
loop_
_publ_author_name
'Mizojiri, Ryo'
'Takami, Kazuaki'
'Ito, Tatsuya'
'Maeda, Hiroyuki'
'Yamano, Mitsuhisa'
'Kawamoto, Tetsuji'
_publ_section_title
;
 Efficient and Stereoselective Syntheses of Isomerically Pure
 4-Aminotetrahydro-2H-thiopyran 1-Oxide Derivatives
;
_journal_issue                   7
_journal_name_full               'Organic Process Research & Development'
_journal_page_first              1034
_journal_paper_doi               10.1021/acs.oprd.7b00147
_journal_volume                  21
_journal_year                    2017
_chemical_formula_moiety         'C11 H14 N2 O5 S2 '
_chemical_formula_sum            'C11 H14 N2 O5 S2'
_chemical_formula_weight         318.36
_chemical_name_systematic
;
cis-2-Nitro-N-(1-oxidotetrahydro-2H-thiopyran-4-yl)benzenesulfonamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.411(3)
_cell_length_b                   14.986(4)
_cell_length_c                   19.855(6)
_cell_measurement_reflns_used    25992
_cell_measurement_temperature    100.2
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      3.0
_cell_volume                     2800.2(14)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.00
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  ' graphite '
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5419
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.4649
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            28975
_diffrn_reflns_theta_max         68.12
_exptl_absorpt_coefficient_mu    3.659
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_correction_T_min  0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       0.0000
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.177
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     181
_refine_ls_number_reflns         438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.177
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0010P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                438
_reflns_number_total             2468
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            op7b00147_si_003.cif
_cod_data_source_block           compound_4a
_cod_original_cell_volume        2800(5)
_cod_original_formula_sum        'C11 H14 N2 O5 S2 '
_cod_database_code               1546762
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
1/2-x,-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,z
x,1/2-y,1/2+z
1/2+x,y,1/2-z
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_calc_flag
C(1) C 0.3079(3) 0.5303(2) 0.6427(1) 0.0134(5) Uani 1.00 d
C(2) C 0.3659(3) 0.4683(2) 0.6876(1) 0.0122(5) Uani 1.00 d
C(3) C 0.4572(3) 0.4991(2) 0.7376(1) 0.0151(6) Uani 1.00 d
C(4) C 0.4881(3) 0.5890(2) 0.7424(1) 0.0180(6) Uani 1.00 d
C(5) C 0.4264(3) 0.6497(2) 0.6988(1) 0.0180(6) Uani 1.00 d
C(6) C 0.3359(3) 0.6208(2) 0.6478(1) 0.0164(6) Uani 1.00 d
N(7) N 0.2144(3) 0.5024(2) 0.5864(1) 0.0192(5) Uani 1.00 d
O(8) O 0.0901(2) 0.5262(1) 0.5886(1) 0.0285(5) Uani 1.00 d
O(9) O 0.2697(2) 0.4603(1) 0.54077(9) 0.0284(5) Uani 1.00 d
S(10) S 0.32351(7) 0.35285(4) 0.68368(3) 0.0127(2) Uani 1.00 d
O(11) O 0.3656(2) 0.3177(1) 0.74811(9) 0.0183(4) Uani 1.00 d
O(12) O 0.1777(2) 0.3466(1) 0.66313(9) 0.0174(4) Uani 1.00 d
N(13) N 0.4181(2) 0.3089(1) 0.6264(1) 0.0144(5) Uani 1.00 d
C(14) C 0.5735(3) 0.3036(2) 0.6288(1) 0.0133(5) Uani 1.00 d
C(15) C 0.6182(3) 0.2126(2) 0.6013(1) 0.0172(6) Uani 1.00 d
C(16) C 0.7781(3) 0.1993(2) 0.6056(1) 0.0220(6) Uani 1.00 d
S(17) S 0.87314(7) 0.27695(5) 0.55269(3) 0.0226(2) Uani 1.00 d
C(18) C 0.8032(3) 0.3771(2) 0.5897(1) 0.0216(6) Uani 1.00 d
C(19) C 0.6411(3) 0.3800(2) 0.5882(1) 0.0179(6) Uani 1.00 d
O(20) O 0.8019(2) 0.2704(1) 0.48466(9) 0.0244(5) Uani 1.00 d
H(3) H 0.4975 0.4591 0.7678 0.0181 Uiso 1.00 calc
H(4) H 0.5509 0.6090 0.7753 0.0216 Uiso 1.00 calc
H(5) H 0.4455 0.7102 0.7036 0.0216 Uiso 1.00 calc
H(6) H 0.2953 0.6612 0.6179 0.0196 Uiso 1.00 calc
H(13) H 0.3755 0.2868 0.5919 0.0173 Uiso 1.00 calc
H(14) H 0.6044 0.3083 0.6758 0.0160 Uiso 1.00 calc
H(15A) H 0.5709 0.1660 0.6267 0.0206 Uiso 1.00 calc
H(15B) H 0.5883 0.2076 0.5547 0.0206 Uiso 1.00 calc
H(16A) H 0.8012 0.1389 0.5920 0.0264 Uiso 1.00 calc
H(16B) H 0.8084 0.2070 0.6519 0.0264 Uiso 1.00 calc
H(18A) H 0.8353 0.3813 0.6360 0.0259 Uiso 1.00 calc
H(18B) H 0.8403 0.4283 0.5655 0.0259 Uiso 1.00 calc
H(19A) H 0.6091 0.3764 0.5418 0.0215 Uiso 1.00 calc
H(19B) H 0.6091 0.4366 0.6064 0.0215 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_publ_flag
C(2) C(1) C(6) 122.1(2) yes
C(2) C(1) N(7) 121.6(2) yes
C(6) C(1) N(7) 116.3(2) yes
C(1) C(2) C(3) 118.3(2) yes
C(1) C(2) S(10) 122.1(2) yes
C(3) C(2) S(10) 119.6(2) yes
C(2) C(3) C(4) 120.2(2) yes
C(3) C(4) C(5) 120.6(2) yes
C(4) C(5) C(6) 120.6(2) yes
C(1) C(6) C(5) 118.2(2) yes
C(1) N(7) O(8) 117.3(2) yes
C(1) N(7) O(9) 116.9(2) yes
O(8) N(7) O(9) 125.8(2) yes
C(2) S(10) O(11) 104.8(1) yes
C(2) S(10) O(12) 106.9(1) yes
C(2) S(10) N(13) 108.0(1) yes
O(11) S(10) O(12) 119.5(1) yes
O(11) S(10) N(13) 109.3(1) yes
O(12) S(10) N(13) 107.8(1) yes
S(10) N(13) C(14) 124.0(2) yes
N(13) C(14) C(15) 108.1(2) yes
N(13) C(14) C(19) 110.8(2) yes
C(15) C(14) C(19) 111.3(2) yes
C(14) C(15) C(16) 111.6(2) yes
C(15) C(16) S(17) 112.0(2) yes
C(16) S(17) C(18) 96.9(1) yes
C(16) S(17) O(20) 105.0(1) yes
C(18) S(17) O(20) 104.9(1) yes
S(17) C(18) C(19) 112.4(2) yes
C(14) C(19) C(18) 112.4(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(2) 1.399(4) yes
C(1) C(6) 1.385(4) yes
C(1) N(7) 1.483(3) yes
C(2) C(3) 1.391(4) yes
C(2) S(10) 1.777(3) yes
C(3) C(4) 1.382(4) yes
C(4) C(5) 1.383(4) yes
C(5) C(6) 1.393(4) yes
N(7) O(8) 1.224(3) yes
N(7) O(9) 1.221(3) yes
S(10) O(11) 1.439(2) yes
S(10) O(12) 1.435(2) yes
S(10) N(13) 1.588(2) yes
N(13) C(14) 1.466(3) yes
C(14) C(15) 1.528(4) yes
C(14) C(19) 1.538(4) yes
C(15) C(16) 1.520(4) yes
C(16) S(17) 1.804(3) yes
S(17) C(18) 1.796(3) yes
S(17) O(20) 1.511(2) yes
C(18) C(19) 1.527(4) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
C(5) O(12) 3.189(3) 6_555
C(5) O(11) 3.359(3) 3_656
C(5) C(16) 3.423(4) 6_655
C(6) O(20) 3.355(3) 5_666
C(6) O(12) 3.399(3) 6_555
O(8) C(15) 3.422(3) 6_555
O(8) C(18) 3.504(3) 1_455
O(8) O(20) 3.528(3) 5_666
O(9) O(20) 3.507(3) 2_456
O(11) C(18) 3.393(3) 8_456
O(11) O(12) 3.452(3) 8_556
O(11) C(16) 3.502(3) 8_456
N(13) O(20) 2.733(3) 2_456
C(14) O(20) 3.583(3) 2_456
C(15) O(20) 3.440(3) 2_456
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_publ_flag
C(1) C(2) C(3) C(4) 0.4(4) yes
C(1) C(2) S(10) O(11) -162.5(2) yes
C(1) C(2) S(10) O(12) -34.8(2) yes
C(1) C(2) S(10) N(13) 81.0(2) yes
C(1) C(6) C(5) C(4) 1.0(4) yes
C(2) C(1) C(6) C(5) 0.9(4) yes
C(2) C(1) N(7) O(8) 113.6(3) yes
C(2) C(1) N(7) O(9) -68.8(3) yes
C(2) C(3) C(4) C(5) 1.5(4) yes
C(2) S(10) N(13) C(14) 64.0(2) yes
C(3) C(2) C(1) C(6) -1.6(4) yes
C(3) C(2) C(1) N(7) 177.5(2) yes
C(3) C(2) S(10) O(11) 16.0(2) yes
C(3) C(2) S(10) O(12) 143.8(2) yes
C(3) C(2) S(10) N(13) -100.5(2) yes
C(3) C(4) C(5) C(6) -2.3(4) yes
C(4) C(3) C(2) S(10) -178.2(2) yes
C(5) C(6) C(1) N(7) -178.3(2) yes
C(6) C(1) C(2) S(10) 176.9(2) yes
C(6) C(1) N(7) O(8) -67.2(3) yes
C(6) C(1) N(7) O(9) 110.4(3) yes
N(7) C(1) C(2) S(10) -3.9(3) yes
S(10) N(13) C(14) C(15) 140.4(2) yes
S(10) N(13) C(14) C(19) -97.4(2) yes
O(11) S(10) N(13) C(14) -49.5(2) yes
O(12) S(10) N(13) C(14) 179.2(2) yes
N(13) C(14) C(15) C(16) -176.8(2) yes
N(13) C(14) C(19) C(18) 179.7(2) yes
C(14) C(15) C(16) S(17) -64.7(2) yes
C(14) C(19) C(18) S(17) 61.9(2) yes
C(15) C(14) C(19) C(18) -59.9(3) yes
C(15) C(16) S(17) C(18) 57.6(2) yes
C(15) C(16) S(17) O(20) -49.9(2) yes
C(16) C(15) C(14) C(19) 61.3(3) yes
C(16) S(17) C(18) C(19) -56.1(2) yes
C(19) C(18) S(17) O(20) 51.4(2) yes
C(19) C(18) S(17) O(20) 51.4(2) yes
