#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:35:49 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296677 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160159.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_7160159
loop_
_publ_author_name
'Zhang, Mengcheng'
'Chen, Yuying'
'Yan, Xiaoyu'
'Zhang, Yonggang'
'Ma, Xiantao'
_publ_section_title
;
 Synthesis of hydroxy-thiazoline substituted pyridine derivatives
 via [3 + 2] annulation of 1,4-dithiane-2,5-diol with
 cyanopyridine.
;
_journal_issue                   42
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8511
_journal_page_last               8515
_journal_paper_doi               10.1039/d4ob01388c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C8 H8 N2 O S'
_chemical_formula_sum            'C8 H8 N2 O S'
_chemical_formula_weight         180.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-15
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-07-17 deposited with the CCDC.	2024-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.975(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0399(3)
_cell_length_b                   15.0255(11)
_cell_length_c                   11.3318(9)
_cell_measurement_reflns_used    9260
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.25
_cell_volume                     856.06(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12362
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.255
_diffrn_source_current           20.0
_diffrn_source_power             0.9
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0748 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.8892.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0466P)²+0.1588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1826
_reflns_number_total             2110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01388c2.cif
_cod_data_source_block           q
_cod_depositor_comments          'Adding full bibliography for 7160159.cif.'
_cod_database_code               7160159
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.45821(7) 0.42184(2) 0.84512(3) 0.05414(14) Uani 1 1 d . . . . .
O1 O 0.5249(3) 0.57699(7) 0.63432(12) 0.0725(4) Uani 1 1 d . . . . .
H1 H 0.502063 0.581087 0.562167 0.109 Uiso 1 1 calc R U . . .
N1 N 0.0764(2) 0.28766(8) 0.77122(10) 0.0513(3) Uani 1 1 d . . . . .
N2 N 0.5205(2) 0.42195(7) 0.61778(12) 0.0533(3) Uani 1 1 d . . . . .
C1 C 0.2069(2) 0.31058(8) 0.67732(10) 0.0416(3) Uani 1 1 d . . . . .
C2 C 0.1659(3) 0.26979(10) 0.56817(12) 0.0540(3) Uani 1 1 d . . . . .
H2 H 0.261844 0.287145 0.504823 0.065 Uiso 1 1 calc R U . . .
C3 C -0.0204(3) 0.20280(10) 0.55566(13) 0.0599(4) Uani 1 1 d . . . . .
H3 H -0.053187 0.174186 0.483341 0.072 Uiso 1 1 calc R U . . .
C4 C -0.1575(3) 0.17878(10) 0.65149(14) 0.0568(3) Uani 1 1 d . . . . .
H4 H -0.284263 0.133747 0.645226 0.068 Uiso 1 1 calc R U . . .
C5 C -0.1032(3) 0.22260(10) 0.75637(14) 0.0580(3) Uani 1 1 d . . . . .
H5 H -0.196680 0.206113 0.820846 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3996(2) 0.38382(8) 0.69867(11) 0.0435(3) Uani 1 1 d . . . . .
C7 C 0.7162(3) 0.49333(11) 0.79707(17) 0.0665(4) Uani 1 1 d . . . . .
H7A H 0.705160 0.551707 0.832936 0.080 Uiso 1 1 calc R U . . .
H7B H 0.890037 0.468306 0.819142 0.080 Uiso 1 1 calc R U . . .
C8 C 0.6724(3) 0.50003(10) 0.66361(16) 0.0635(4) Uani 1 1 d . . . . .
H8 H 0.844253 0.502622 0.628203 0.076 Uiso 1 1 calc R U . . .
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
C6 S1 C7 89.19(7) . . ?
C8 O1 H1 109.5 . . ?
C1 N1 C5 117.12(12) . . ?
C6 N2 C8 111.55(13) . . ?
N1 C1 C2 123.21(12) . . ?
N1 C1 C6 114.62(11) . . ?
C2 C1 C6 122.17(11) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.31(13) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.14(13) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.56(13) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 123.66(13) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N2 C6 S1 118.42(10) . . ?
N2 C6 C1 124.07(12) . . ?
C1 C6 S1 117.50(9) . . ?
S1 C7 H7A 110.4 . . ?
S1 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 S1 106.45(10) . . ?
C8 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
O1 C8 N2 108.57(13) . . ?
O1 C8 C7 109.20(13) . . ?
O1 C8 H8 109.8 . . ?
N2 C8 C7 109.53(12) . . ?
N2 C8 H8 109.8 . . ?
C7 C8 H8 109.8 . . ?
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 C6 1.7606(13) . ?
S1 C7 1.7998(16) . ?
O1 H1 0.8200 . ?
O1 C8 1.4023(19) . ?
N1 C1 1.3341(16) . ?
N1 C5 1.3351(18) . ?
N2 C6 1.2716(16) . ?
N2 C8 1.4755(19) . ?
C1 C2 1.3831(18) . ?
C1 C6 1.4768(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(2) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.517(3) . ?
C8 H8 0.9800 . ?
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
S1 C7 C8 O1 95.59(13) . . . . ?
S1 C7 C8 N2 -23.19(14) . . . . ?
N1 C1 C2 C3 0.6(2) . . . . ?
N1 C1 C6 S1 6.84(15) . . . . ?
N1 C1 C6 N2 -171.61(12) . . . . ?
C1 N1 C5 C4 0.4(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C1 C6 S1 -173.39(11) . . . . ?
C2 C1 C6 N2 8.2(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 N1 -0.1(3) . . . . ?
C5 N1 C1 C2 -0.7(2) . . . . ?
C5 N1 C1 C6 179.07(12) . . . . ?
C6 S1 C7 C8 16.85(11) . . . . ?
C6 N2 C8 O1 -99.97(14) . . . . ?
C6 N2 C8 C7 19.20(17) . . . . ?
C6 C1 C2 C3 -179.12(13) . . . . ?
C7 S1 C6 N2 -7.18(12) . . . . ?
C7 S1 C6 C1 174.28(10) . . . . ?
C8 N2 C6 S1 -5.95(16) . . . . ?
C8 N2 C6 C1 172.48(12) . . . . ?
