#------------------------------------------------------------------------------
#$Date: 2022-02-03 23:25:43 +0200 (Thu, 03 Feb 2022) $
#$Revision: 272482 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519311.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_4519311
loop_
_publ_author_name
'Oh, In Seok'
'Seo, Ye Ji'
'Hyun, Ji Young'
'Lim, Hwan Jung'
'Lee, Duck-Hyung'
'Park, Seong Jun'
_publ_section_title
;
 Acid-Catalyzed Hydrolysis and Intramolecular Cyclization of
 N-Cyano Sulfoximines for the Synthesis of Thiadiazine 1-Oxides.
;
_journal_issue                   2
_journal_name_full               'ACS omega'
_journal_page_first              2160
_journal_page_last               2169
_journal_paper_doi               10.1021/acsomega.1c05570
_journal_volume                  7
_journal_year                    2022
_chemical_formula_sum            'C15 H15 N3 O3 S'
_chemical_formula_weight         317.36
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.4990(10)
_cell_angle_beta                 83.0080(10)
_cell_angle_gamma                67.8340(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6805(2)
_cell_length_b                   9.2760(2)
_cell_length_c                   10.4682(2)
_cell_measurement_reflns_used    3946
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      24.87
_cell_measurement_theta_min      2.43
_cell_volume                     755.39(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3744
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.9641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0501
_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)+(0.0778P)²+0.0543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                2828
_reflns_number_total             3744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao1c05570_si_002.cif
_cod_data_source_block           20190306_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4519311
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.41757(5) 0.26101(5) 0.08897(4) 0.04031(16) Uani 1 1 d . . .
O1 O 0.42801(16) 0.40094(16) 0.11855(14) 0.0520(3) Uani 1 1 d . . .
O2 O 0.40760(15) 0.15337(15) 0.35593(12) 0.0501(3) Uani 1 1 d . . .
O3 O -0.11555(16) 0.66207(16) 0.25849(15) 0.0593(4) Uani 1 1 d . . .
N1 N 0.53692(17) 0.09377(17) 0.15812(14) 0.0423(3) Uani 1 1 d . . .
N2 N 0.61954(19) -0.08049(19) 0.35596(15) 0.0525(4) Uani 1 1 d . . .
H2A H 0.6148 -0.1101 0.4406 0.063 Uiso 1 1 calc R . .
H2B H 0.6922 -0.1420 0.3106 0.063 Uiso 1 1 calc R . .
N3 N 0.12994(18) 0.45497(18) 0.25779(16) 0.0488(4) Uani 1 1 d . . .
H3A H 0.2294 0.4143 0.2866 0.059 Uiso 1 1 calc R . .
C1 C 0.2062(2) 0.2735(2) 0.10773(17) 0.0389(4) Uani 1 1 d . . .
C2 C 0.0868(2) 0.3684(2) 0.18509(18) 0.0412(4) Uani 1 1 d . . .
C3 C -0.0744(2) 0.3696(2) 0.1919(2) 0.0551(5) Uani 1 1 d . . .
H3B H -0.1547 0.4294 0.2446 0.066 Uiso 1 1 calc R . .
C4 C -0.1172(3) 0.2834(3) 0.1217(3) 0.0640(6) Uani 1 1 d . . .
H4A H -0.2264 0.2877 0.1258 0.077 Uiso 1 1 calc R . .
C5 C -0.0006(3) 0.1919(3) 0.0463(2) 0.0617(6) Uani 1 1 d . . .
H5A H -0.0306 0.1345 -0.0009 0.074 Uiso 1 1 calc R . .
C6 C 0.1607(3) 0.1846(2) 0.0402(2) 0.0509(5) Uani 1 1 d . . .
H6A H 0.2404 0.1198 -0.0094 0.061 Uiso 1 1 calc R . .
C7 C 0.4717(3) 0.2632(3) -0.07903(19) 0.0568(5) Uani 1 1 d . . .
H7A H 0.5851 0.2566 -0.0953 0.085 Uiso 1 1 calc R . .
H7B H 0.4000 0.3605 -0.1323 0.085 Uiso 1 1 calc R . .
H7C H 0.4594 0.1737 -0.1010 0.085 Uiso 1 1 calc R . .
C8 C 0.5147(2) 0.0601(2) 0.29532(17) 0.0405(4) Uani 1 1 d . . .
C9 C 0.0313(2) 0.5958(2) 0.28724(18) 0.0445(4) Uani 1 1 d . . .
C10 C 0.1158(2) 0.6693(2) 0.3536(2) 0.0495(5) Uani 1 1 d . . .
C11 C 0.2381(3) 0.5803(3) 0.4440(2) 0.0686(6) Uani 1 1 d . . .
H11A H 0.2732 0.4695 0.4646 0.082 Uiso 1 1 calc R . .
C12 C 0.3086(3) 0.6570(4) 0.5043(3) 0.0836(8) Uani 1 1 d . . .
H12A H 0.3884 0.5974 0.5677 0.100 Uiso 1 1 calc R . .
C13 C 0.2611(4) 0.8207(4) 0.4708(3) 0.0842(8) Uani 1 1 d . . .
H13A H 0.3124 0.8710 0.5087 0.101 Uiso 1 1 calc R . .
C14 C 0.1388(4) 0.9094(3) 0.3819(3) 0.0818(8) Uani 1 1 d . . .
H14A H 0.1054 1.0201 0.3603 0.098 Uiso 1 1 calc R . .
C15 C 0.0657(3) 0.8349(3) 0.3247(2) 0.0652(6) Uani 1 1 d . . .
H15A H -0.0190 0.8959 0.2656 0.078 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 118.77(8) . . ?
O1 S1 C7 108.73(9) . . ?
N1 S1 C7 102.22(8) . . ?
O1 S1 C1 109.13(8) . . ?
N1 S1 C1 111.40(8) . . ?
C7 S1 C1 105.58(9) . . ?
C8 N1 S1 113.49(11) . . ?
C8 N2 H2A 120.0 . . ?
C8 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C9 N3 C2 126.73(15) . . ?
C9 N3 H3A 116.6 . . ?
C2 N3 H3A 116.6 . . ?
C6 C1 C2 119.79(16) . . ?
C6 C1 S1 117.08(13) . . ?
C2 C1 S1 123.12(13) . . ?
C3 C2 N3 120.64(16) . . ?
C3 C2 C1 118.17(16) . . ?
N3 C2 C1 121.15(15) . . ?
C4 C3 C2 120.90(19) . . ?
C4 C3 H3B 119.6 . . ?
C2 C3 H3B 119.6 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.03(19) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 120.51(18) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N2 122.63(16) . . ?
O2 C8 N1 123.30(16) . . ?
N2 C8 N1 114.07(14) . . ?
O3 C9 N3 123.21(17) . . ?
O3 C9 C10 121.73(16) . . ?
N3 C9 C10 115.02(16) . . ?
C11 C10 C15 119.0(2) . . ?
C11 C10 C9 122.72(19) . . ?
C15 C10 C9 118.3(2) . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15A 119.5 . . ?
C10 C15 H15A 119.5 . . ?
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 1.4442(13) . ?
S1 N1 1.5528(15) . ?
S1 C7 1.7612(19) . ?
S1 C1 1.7843(18) . ?
O2 C8 1.241(2) . ?
O3 C9 1.226(2) . ?
N1 C8 1.397(2) . ?
N2 C8 1.328(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C9 1.352(2) . ?
N3 C2 1.402(2) . ?
N3 H3A 0.8600 . ?
C1 C6 1.393(2) . ?
C1 C2 1.403(2) . ?
C2 C3 1.389(3) . ?
C3 C4 1.380(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.363(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.370(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.492(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.391(3) . ?
C11 C12 1.387(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.377(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.368(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.367(3) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.86 2.07 2.9215(19) 173.4 2_656
N2 H2B O3 0.86 2.09 2.922(2) 162.2 1_645
N3 H3A O1 0.86 2.30 2.7459(19) 112.4 .
N3 H3A O2 0.86 2.31 2.961(2) 132.4 .
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 62.25(15) . . . . ?
C7 S1 N1 C8 -178.17(13) . . . . ?
C1 S1 N1 C8 -65.83(14) . . . . ?
O1 S1 C1 C6 157.40(14) . . . . ?
N1 S1 C1 C6 -69.51(16) . . . . ?
C7 S1 C1 C6 40.68(17) . . . . ?
O1 S1 C1 C2 -21.97(18) . . . . ?
N1 S1 C1 C2 111.12(16) . . . . ?
C7 S1 C1 C2 -138.69(16) . . . . ?
C9 N3 C2 C3 -33.6(3) . . . . ?
C9 N3 C2 C1 148.94(19) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
S1 C1 C2 C3 179.62(15) . . . . ?
C6 C1 C2 N3 177.82(17) . . . . ?
S1 C1 C2 N3 -2.8(3) . . . . ?
N3 C2 C3 C4 -179.33(19) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
S1 C1 C6 C5 -177.92(16) . . . . ?
S1 N1 C8 O2 1.4(2) . . . . ?
S1 N1 C8 N2 -177.98(13) . . . . ?
C2 N3 C9 O3 4.1(3) . . . . ?
C2 N3 C9 C10 -173.65(17) . . . . ?
O3 C9 C10 C11 145.9(2) . . . . ?
N3 C9 C10 C11 -36.3(3) . . . . ?
O3 C9 C10 C15 -32.6(3) . . . . ?
N3 C9 C10 C15 145.24(19) . . . . ?
C15 C10 C11 C12 0.0(3) . . . . ?
C9 C10 C11 C12 -178.5(2) . . . . ?
C10 C11 C12 C13 -2.3(4) . . . . ?
C11 C12 C13 C14 2.8(4) . . . . ?
C12 C13 C14 C15 -1.1(4) . . . . ?
C13 C14 C15 C10 -1.2(4) . . . . ?
C11 C10 C15 C14 1.8(3) . . . . ?
C9 C10 C15 C14 -179.7(2) . . . . ?
