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#$Date: 2024-02-04 13:02:26 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289327 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/23/7132384.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_7132384
loop_
_publ_author_name
'Bhat, Showkat Ahmad'
'Ahmed, Qazi Naveed'
'Bhat, Khursheed Ahmad'
_publ_section_title
;
 DMSO-KOH mediated stereoselective synthesis of Z-enamides: an
 expeditious route to Z-enamide bearing natural products.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              114
_journal_page_last               117
_journal_paper_doi               10.1039/d3cc04642g
_journal_volume                  60
_journal_year                    2023
_chemical_formula_moiety         'C12 H12 O3 S'
_chemical_formula_sum            'C12 H12 O3 S'
_chemical_formula_weight         236.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2ffhcr
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-08 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.067(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6096(16)
_cell_length_b                   8.7670(15)
_cell_length_c                   14.390(3)
_cell_measurement_reflns_used    9402
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.68
_cell_measurement_theta_min      2.32
_cell_volume                     1176.0(4)
_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-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44612
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.849
_diffrn_reflns_theta_min         2.314
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.5966
_exptl_absorpt_correction_T_min  0.5528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         4326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0693P)²+0.1695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3819
_reflns_number_total             4326
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04642g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7132384.cif.'
_cod_original_cell_volume        1176.0(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7132384
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.88997(3) 0.89978(3) 0.36612(2) 0.04460(10) Uani 1 1 d . . . . .
O1 O 0.62769(8) 0.88077(8) 0.46830(5) 0.03394(16) Uani 1 1 d . . . . .
O2 O 0.55561(8) 0.54286(9) 0.39430(6) 0.03672(17) Uani 1 1 d . . . . .
O3 O 0.72738(10) 0.36452(8) 0.41616(7) 0.04324(19) Uani 1 1 d . . . . .
C1 C 0.51035(9) 0.85821(9) 0.30378(6) 0.02386(15) Uani 1 1 d . . . . .
C2 C 0.51156(10) 0.79067(11) 0.21636(6) 0.03043(18) Uani 1 1 d . . . . .
H2A H 0.591681 0.731606 0.210141 0.037 Uiso 1 1 calc R U . . .
C3 C 0.39533(12) 0.80994(14) 0.13836(7) 0.0398(2) Uani 1 1 d . . . . .
H3A H 0.394826 0.761961 0.079089 0.048 Uiso 1 1 calc R U . . .
C4 C 0.27999(12) 0.89916(14) 0.14689(8) 0.0417(2) Uani 1 1 d . . . . .
H4A H 0.200346 0.911641 0.093480 0.050 Uiso 1 1 calc R U . . .
C5 C 0.28030(10) 0.97038(14) 0.23317(8) 0.0386(2) Uani 1 1 d . . . . .
H5A H 0.202477 1.034147 0.238080 0.046 Uiso 1 1 calc R U . . .
C6 C 0.39438(10) 0.94835(11) 0.31220(7) 0.03046(17) Uani 1 1 d . . . . .
H6A H 0.393502 0.994459 0.371794 0.037 Uiso 1 1 calc R U . . .
C7 C 0.62985(9) 0.83418(9) 0.38918(5) 0.02352(15) Uani 1 1 d . . . . .
C8 C 0.76725(8) 0.76030(10) 0.37698(5) 0.02471(15) Uani 1 1 d . . . . .
C9 C 1.04847(15) 0.7919(3) 0.36831(17) 0.0840(6) Uani 1 1 d . . . . .
H9A H 1.126827 0.861402 0.364576 0.126 Uiso 1 1 calc R U . . .
H9B H 1.030392 0.721975 0.313565 0.126 Uiso 1 1 calc R U . . .
H9C H 1.075129 0.733282 0.427975 0.126 Uiso 1 1 calc R U . . .
C10 C 0.79045(9) 0.60945(10) 0.38232(6) 0.02812(17) Uani 1 1 d . . . . .
H10A H 0.879918 0.569431 0.376711 0.034 Uiso 1 1 calc R U . . .
C11 C 0.67754(10) 0.50634(10) 0.39682(6) 0.02855(17) Uani 1 1 d . . . . .
C12 C 0.62325(18) 0.25853(14) 0.43777(14) 0.0632(4) Uani 1 1 d . . . . .
H12A H 0.667978 0.158180 0.452805 0.095 Uiso 1 1 calc R U . . .
H12B H 0.541262 0.249890 0.382152 0.095 Uiso 1 1 calc R U . . .
H12C H 0.590293 0.296064 0.492911 0.095 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'
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_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.3c00306 2023
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
C8 S1 C9 102.77(7) . . ?
C11 O3 C12 114.11(10) . . ?
C2 C1 C6 120.08(8) . . ?
C2 C1 C7 120.97(8) . . ?
C6 C1 C7 118.94(7) . . ?
C3 C2 C1 119.79(9) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C4 C3 C2 120.05(10) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.31(9) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 119.96(9) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 119.75(9) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
O1 C7 C1 122.97(8) . . ?
O1 C7 C8 117.73(7) . . ?
C1 C7 C8 119.08(7) . . ?
C10 C8 C7 123.46(8) . . ?
C10 C8 S1 126.47(7) . . ?
C7 C8 S1 109.84(6) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 119.88(8) . . ?
C8 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
O2 C11 O3 123.30(9) . . ?
O2 C11 C10 125.39(8) . . ?
O3 C11 C10 111.29(8) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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 C8 1.7321(9) . ?
S1 C9 1.7865(17) . ?
O1 C7 1.2145(10) . ?
O2 C11 1.2067(12) . ?
O3 C11 1.3371(11) . ?
O3 C12 1.4535(16) . ?
C1 C2 1.3930(12) . ?
C1 C6 1.3952(12) . ?
C1 C7 1.4790(11) . ?
C2 C3 1.3879(13) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3862(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3891(17) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3879(13) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.5187(12) . ?
C8 C10 1.3403(12) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4656(13) . ?
C10 H10A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
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
_geom_hbond_publ_flag
C12 H12A O1 0.98 2.48 3.3397(15) 146.1 1_545 yes
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
C6 C1 C2 C3 -1.74(14) . . . . ?
C7 C1 C2 C3 177.34(9) . . . . ?
C1 C2 C3 C4 1.55(16) . . . . ?
C2 C3 C4 C5 0.37(18) . . . . ?
C3 C4 C5 C6 -2.10(17) . . . . ?
C4 C5 C6 C1 1.89(16) . . . . ?
C2 C1 C6 C5 0.02(14) . . . . ?
C7 C1 C6 C5 -179.08(9) . . . . ?
C2 C1 C7 O1 -173.93(9) . . . . ?
C6 C1 C7 O1 5.16(13) . . . . ?
C2 C1 C7 C8 11.57(11) . . . . ?
C6 C1 C7 C8 -169.35(8) . . . . ?
O1 C7 C8 C10 94.82(10) . . . . ?
C1 C7 C8 C10 -90.39(10) . . . . ?
O1 C7 C8 S1 -80.06(8) . . . . ?
C1 C7 C8 S1 94.73(7) . . . . ?
C9 S1 C8 C10 -1.89(12) . . . . ?
C9 S1 C8 C7 172.80(9) . . . . ?
C7 C8 C10 C11 2.54(13) . . . . ?
S1 C8 C10 C11 176.56(6) . . . . ?
C12 O3 C11 O2 -2.32(16) . . . . ?
C12 O3 C11 C10 176.03(10) . . . . ?
C8 C10 C11 O2 8.65(14) . . . . ?
C8 C10 C11 O3 -169.66(8) . . . . ?
