#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/70/1507026.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_1507026
loop_
_publ_author_name
'Dong, Chune'
'Alper, Howard'
_publ_section_title
;
 Highly regioselective synthesis of tetrahydro-2H-1,3-thiazin-2-ones via
 rhodium-catalyzed carbonylation of N-alkylisothiazolidines.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              3489
_journal_page_last               3492
_journal_paper_doi               10.1021/ol048706b
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C12 H15 N O2 S'
_chemical_formula_weight         237.31
_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                 92.236(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.640(3)
_cell_length_b                   5.7416(7)
_cell_length_c                   9.5059(12)
_cell_measurement_reflns_used    961
_cell_measurement_temperature    206(2)
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      2.83
_cell_volume                     1180.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      206(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7653
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.
_exptl_absorpt_correction_T_min  .9
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0609
_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)+(0.0539P)²+0.6682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                1627
_reflns_number_total             2398
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048706bsi20040707_114912.cif
_cod_data_source_block           ha403
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-Scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507026
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32426(11) 0.2656(4) -0.0741(3) 0.0722(7) Uani 1 1 d . . .
C2 C 0.34604(13) 0.4036(5) 0.0115(3) 0.0398(7) Uani 1 1 d . A .
S3 S 0.42400(4) 0.35126(15) 0.06663(10) 0.0581(3) Uani 1 1 d . . .
C4 C 0.4409(4) 0.5408(13) 0.2122(10) 0.060(2) Uani 0.603(11) 1 d PDU A 1
H4A H 0.4310 0.4617 0.2999 0.073 Uiso 0.603(11) 1 calc PR A 1
H4B H 0.4852 0.5771 0.2165 0.073 Uiso 0.603(11) 1 calc PR A 1
C5 C 0.4051(2) 0.7591(11) 0.1996(12) 0.064(2) Uani 0.603(11) 1 d PDU A 1
H5A H 0.4114 0.8435 0.2886 0.076 Uiso 0.603(11) 1 calc PR A 1
H5B H 0.4240 0.8533 0.1267 0.076 Uiso 0.603(11) 1 calc PR A 1
C4B C 0.4446(4) 0.631(2) 0.1609(10) 0.044(3) Uani 0.397(11) 1 d PDU A 2
H4BA H 0.4832 0.6130 0.2172 0.053 Uiso 0.397(11) 1 calc PR A 2
H4BB H 0.4496 0.7577 0.0934 0.053 Uiso 0.397(11) 1 calc PR A 2
C5B C 0.3926(3) 0.6794(18) 0.2525(7) 0.040(3) Uani 0.397(11) 1 d PDU A 2
H5BA H 0.3827 0.5389 0.3056 0.048 Uiso 0.397(11) 1 calc PR A 2
H5BB H 0.4044 0.8021 0.3199 0.048 Uiso 0.397(11) 1 calc PR A 2
C6 C 0.33796(13) 0.7539(6) 0.1667(4) 0.0570(9) Uani 1 1 d D . .
H6A H 0.3171 0.7195 0.2539 0.068 Uiso 1 1 calc R A 1
H6B H 0.3252 0.9106 0.1368 0.068 Uiso 1 1 calc R A 1
N7 N 0.31532(9) 0.5893(4) 0.0592(2) 0.0342(5) Uani 1 1 d . A .
C8 C 0.25254(12) 0.6359(6) 0.0026(3) 0.0462(7) Uani 1 1 d . . .
H8A H 0.2449 0.5405 -0.0818 0.055 Uiso 1 1 calc R A .
H8B H 0.2498 0.7997 -0.0259 0.055 Uiso 1 1 calc R . .
C9 C 0.20252(11) 0.5860(5) 0.1058(3) 0.0326(6) Uani 1 1 d . A .
C10 C 0.15247(12) 0.7364(5) 0.1152(3) 0.0365(6) Uani 1 1 d . . .
H10A H 0.1513 0.8734 0.0610 0.044 Uiso 1 1 calc R A .
C11 C 0.10436(12) 0.6892(5) 0.2021(3) 0.0359(7) Uani 1 1 d . A .
H11A H 0.0709 0.7930 0.2063 0.043 Uiso 1 1 calc R . .
C12 C 0.10549(11) 0.4882(5) 0.2836(2) 0.0287(6) Uani 1 1 d . . .
C13 C 0.15563(12) 0.3389(5) 0.2790(3) 0.0365(6) Uani 1 1 d . A .
H13A H 0.1574 0.2047 0.3356 0.044 Uiso 1 1 calc R . .
C14 C 0.20354(12) 0.3890(5) 0.1897(3) 0.0388(7) Uani 1 1 d . . .
H14A H 0.2373 0.2865 0.1865 0.047 Uiso 1 1 calc R A .
O15 O 0.05520(8) 0.4549(3) 0.36571(18) 0.0399(5) Uani 1 1 d . A .
C16 C 0.05415(13) 0.2485(5) 0.4496(3) 0.0449(7) Uani 1 1 d . . .
H16A H 0.0183 0.2517 0.5078 0.067 Uiso 1 1 calc R A .
H16B H 0.0915 0.2407 0.5093 0.067 Uiso 1 1 calc R . .
H16C H 0.0519 0.1130 0.3887 0.067 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
O1 C2 N7 123.9(3)
O1 C2 S3 115.2(2)
N7 C2 S3 120.8(2)
C2 S3 C4 106.8(2)
C2 S3 C4B 101.6(4)
C4 S3 C4B 22.3(3)
C5 C4 S3 111.3(6)
C6 C5 C4 120.6(6)
C5B C4B S3 105.7(7)
C6 C5B C4B 110.0(6)
N7 C6 C5B 116.0(4)
N7 C6 C5 117.5(4)
C5B C6 C5 29.0(3)
C2 N7 C6 126.3(2)
C2 N7 C8 118.9(2)
C6 N7 C8 114.8(2)
N7 C8 C9 113.7(2)
C14 C9 C10 117.7(2)
C14 C9 C8 122.1(2)
C10 C9 C8 120.1(2)
C11 C10 C9 121.6(2)
C10 C11 C12 119.9(2)
O15 C12 C13 124.7(2)
O15 C12 C11 115.7(2)
C13 C12 C11 119.6(2)
C12 C13 C14 119.5(2)
C9 C14 C13 121.6(2)
C12 O15 C16 117.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.218(3)
C2 N7 1.344(3)
C2 S3 1.773(3)
S3 C4 1.787(8)
S3 C4B 1.883(11)
C4 C5 1.476(4)
C5 C6 1.475(4)
C4B C5B 1.476(4)
C5B C6 1.474(4)
C6 N7 1.462(4)
N7 C8 1.466(3)
C8 C9 1.517(3)
C9 C14 1.383(4)
C9 C10 1.391(4)
C10 C11 1.381(4)
C11 C12 1.389(3)
C12 O15 1.377(3)
C12 C13 1.385(3)
C13 C14 1.395(4)
O15 C16 1.429(3)
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 C2 S3 C4 -170.0(4)
N7 C2 S3 C4 12.3(4)
O1 C2 S3 C4B 167.6(4)
N7 C2 S3 C4B -10.1(4)
C2 S3 C4 C5 -31.1(9)
C4B S3 C4 C5 48.3(8)
S3 C4 C5 C6 48.5(14)
C2 S3 C4B C5B 46.4(7)
C4 S3 C4B C5B -59.8(8)
S3 C4B C5B C6 -72.1(11)
C4B C5B C6 N7 58.4(10)
C4B C5B C6 C5 -41.9(8)
C4 C5 C6 N7 -42.0(13)
C4 C5 C6 C5B 52.7(9)
O1 C2 N7 C6 176.8(3)
S3 C2 N7 C6 -5.7(4)
O1 C2 N7 C8 -2.2(4)
S3 C2 N7 C8 175.31(19)
C5B C6 N7 C2 -15.0(6)
C5 C6 N7 C2 17.6(6)
C5B C6 N7 C8 164.0(4)
C5 C6 N7 C8 -163.4(5)
C2 N7 C8 C9 108.1(3)
C6 N7 C8 C9 -71.0(3)
N7 C8 C9 C14 -42.9(4)
N7 C8 C9 C10 139.3(3)
C14 C9 C10 C11 -1.7(4)
C8 C9 C10 C11 176.2(2)
C9 C10 C11 C12 0.4(4)
C10 C11 C12 O15 -179.3(2)
C10 C11 C12 C13 1.4(4)
O15 C12 C13 C14 179.0(2)
C11 C12 C13 C14 -1.8(4)
C10 C9 C14 C13 1.2(4)
C8 C9 C14 C13 -176.6(3)
C12 C13 C14 C9 0.5(4)
C13 C12 O15 C16 -1.6(4)
C11 C12 O15 C16 179.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101352615
