#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/74/7157448.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_7157448
loop_
_publ_author_name
'Antony Savarimuthu, S.'
'Leo Prakash, D. G.'
'Augustine Thomas, S.'
'Gandhi, Thirumanavelan'
'Bera, Mrinal K.'
_publ_section_title
;
 Highly Z-selective synthesis of 1,3-oxathiol-2-ylidenes and
 4-methylene-oxazolidine-2-thiones via atom-specific 5-exo-dig cyclization
 of propargyl alcohol with isothiocyanate.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3552
_journal_page_last               3562
_journal_paper_doi               10.1039/d0ob00083c
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C17 H13 Cl2 N O S'
_chemical_formula_weight         350.24
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-15 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.066(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.656(4)
_cell_length_b                   21.804(10)
_cell_length_c                   10.011(5)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.461
_cell_measurement_theta_min      2.314
_cell_volume                     1605.9(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1799
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            44307
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.461
_diffrn_reflns_theta_min         2.314
_exptl_absorpt_coefficient_mu    0.534
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.657
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.657
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0538
_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)+(0.1715P)²+2.5619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1703
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2960
_reflns_number_total             3312
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00083c2.cif
_cod_data_source_block           MKB_F_2_0m_a
_cod_depositor_comments
'Adding full bibliography for 7157446--7157448.cif.'
_cod_original_cell_volume        1605.9(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157448
_shelx_shelxl_version_number     2014/7
_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.
;
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 0.39386(8) 0.33043(3) 0.37400(7) 0.0429(2) Uani 1 1 d . . . . .
Cl02 Cl 0.45974(10) 0.49907(4) 0.73788(10) 0.0713(3) Uani 1 1 d . . . . .
Cl03 Cl 0.21867(17) 0.36331(7) -0.06197(13) 0.1136(6) Uani 1 1 d . . . . .
O1 O 0.4505(3) 0.22682(8) 0.2644(2) 0.0532(5) Uani 1 1 d . . . . .
N1 N 0.1876(3) 0.27081(10) 0.1483(2) 0.0528(6) Uani 1 1 d . . . . .
C11 C 0.7625(3) 0.38230(10) 0.5899(2) 0.0326(5) Uani 1 1 d . . . . .
C16 C 0.9214(3) 0.41624(10) 0.6022(2) 0.0336(5) Uani 1 1 d . . . . .
C9 C 0.6028(3) 0.29467(9) 0.4470(2) 0.0367(5) Uani 1 1 d . . . . .
C10 C 0.7475(3) 0.31983(10) 0.5323(3) 0.0378(5) Uani 1 1 d . . . . .
H10 H 0.8512 0.2955 0.5589 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6201(3) 0.40815(11) 0.6321(2) 0.0382(5) Uani 1 1 d . . . . .
H12 H 0.5157 0.3855 0.6273 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0646(3) 0.32017(11) 0.1301(2) 0.0426(6) Uani 1 1 d . . . . .
C14 C 0.7871(3) 0.50223(11) 0.6897(3) 0.0424(5) Uani 1 1 d . . . . .
H14 H 0.7943 0.5425 0.7211 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3285(3) 0.27241(10) 0.2474(2) 0.0398(5) Uani 1 1 d . . . . .
C15 C 0.9288(3) 0.47583(11) 0.6506(3) 0.0404(5) Uani 1 1 d . . . . .
H15 H 1.0330 0.4989 0.6571 0.049 Uiso 1 1 calc R U . . .
C13 C 0.6352(3) 0.46754(11) 0.6809(2) 0.0408(5) Uani 1 1 d . . . . .
C17 C 1.0802(3) 0.38984(12) 0.5609(3) 0.0442(6) Uani 1 1 d . . . . .
H17A H 1.1754 0.4199 0.5758 0.066 Uiso 1 1 calc R U . . .
H17B H 1.0425 0.3786 0.4644 0.066 Uiso 1 1 calc R U . . .
H17C H 1.1241 0.3542 0.6162 0.066 Uiso 1 1 calc R U . . .
C5 C -0.0639(4) 0.32362(14) 0.2028(3) 0.0553(7) Uani 1 1 d . . . . .
H5 H -0.0633 0.2944 0.2706 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5913(4) 0.23018(11) 0.3926(3) 0.0510(6) Uani 1 1 d . . . . .
H8A H 0.7066 0.2184 0.3776 0.061 Uiso 1 1 calc R U . . .
H8B H 0.5649 0.2022 0.4597 0.061 Uiso 1 1 calc R U . . .
C1 C 0.0591(4) 0.36438(14) 0.0307(3) 0.0509(6) Uani 1 1 d . . . . .
C2 C -0.0708(4) 0.40959(15) 0.0038(3) 0.0588(7) Uani 1 1 d . . . . .
H2 H -0.0726 0.4388 -0.0642 0.071 Uiso 1 1 calc R U . . .
C3 C -0.1979(4) 0.41174(15) 0.0768(3) 0.0582(7) Uani 1 1 d . . . . .
H3 H -0.2869 0.4420 0.0580 0.070 Uiso 1 1 calc R U . . .
C4 C -0.1924(4) 0.36900(16) 0.1777(3) 0.0602(7) Uani 1 1 d . . . . .
H4 H -0.2762 0.3707 0.2294 0.072 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'
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
C9 S1 C7 91.46(11) . . ?
C7 O1 C8 113.63(19) . . ?
C7 N1 C6 118.8(2) . . ?
C12 C11 C16 119.6(2) . . ?
C12 C11 C10 120.7(2) . . ?
C16 C11 C10 119.7(2) . . ?
C15 C16 C11 118.5(2) . . ?
C15 C16 C17 119.9(2) . . ?
C11 C16 C17 121.5(2) . . ?
C10 C9 C8 125.4(2) . . ?
C10 C9 S1 126.43(18) . . ?
C8 C9 S1 108.12(17) . . ?
C9 C10 C11 126.9(2) . . ?
C9 C10 H10 116.5 . . ?
C11 C10 H10 116.5 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C1 C6 N1 120.9(3) . . ?
C1 C6 C5 117.4(2) . . ?
N1 C6 C5 121.5(3) . . ?
C15 C14 C13 118.2(2) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
N1 C7 O1 119.9(2) . . ?
N1 C7 S1 127.09(19) . . ?
O1 C7 S1 113.03(17) . . ?
C16 C15 C14 122.3(2) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C12 C13 C14 121.9(2) . . ?
C12 C13 Cl02 119.43(19) . . ?
C14 C13 Cl02 118.67(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
O1 C8 C9 109.1(2) . . ?
O1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
O1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C6 C1 C2 121.3(3) . . ?
C6 C1 Cl03 119.6(2) . . ?
C2 C1 Cl03 119.1(2) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
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 C9 1.747(2) . ?
S1 C7 1.762(2) . ?
Cl02 C13 1.740(2) . ?
Cl03 C1 1.726(3) . ?
O1 C7 1.342(3) . ?
O1 C8 1.431(3) . ?
N1 C7 1.248(3) . ?
N1 C6 1.408(3) . ?
C11 C12 1.392(3) . ?
C11 C16 1.400(3) . ?
C11 C10 1.471(3) . ?
C16 C15 1.383(3) . ?
C16 C17 1.502(3) . ?
C9 C10 1.317(3) . ?
C9 C8 1.502(3) . ?
C10 H10 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C6 C1 1.378(4) . ?
C6 C5 1.379(4) . ?
C14 C15 1.377(4) . ?
C14 C13 1.369(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 C4 1.369(4) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.373(4) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353359
