#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/11/7151167.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_7151167
loop_
_publ_author_name
'Evans, Lyndsay Ann'
'Adams, Harry'
'Barber, Christopher G.'
'Caggiano, Lorenzo'
'Jackson, Richard F. W.'
_publ_section_title
;
 Stereoselective synthesis of 2,3-difunctionalised thioesters using
 nucleophilic epoxidation of 1-arylthio-1-nitroalkenes.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3156
_journal_page_last               3163
_journal_paper_doi               10.1039/b710237b
_journal_volume                  5
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_sum            'C12 H13 N O3 S'
_chemical_formula_weight         251.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.212(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.249(3)
_cell_length_b                   5.794(3)
_cell_length_c                   20.357(12)
_cell_measurement_reflns_used    1541
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.01
_cell_volume                     617.4(6)
_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      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker smart1000'
_diffrn_measurement_method       '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  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6821
_diffrn_reflns_theta_full        27.66
_diffrn_reflns_theta_max         27.66
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.8973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0568
_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)+(0.0515P)²+0.5125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                2263
_reflns_number_total             2777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b710237b.txt
_cod_data_source_block           orj56m
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7151167
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.88103(17) 0.94450(15) 0.28891(5) 0.0264(2) Uani 1 1 d . . .
N1 N 0.6784(7) 1.1608(5) 0.06584(16) 0.0273(8) Uani 1 1 d . . .
H1A H 0.6225 1.1143 0.0262 0.033 Uiso 1 1 calc R . .
O1 O 0.5291(6) 1.5353(5) 0.06025(14) 0.0336(7) Uani 1 1 d . . .
O2 O 0.7495(5) 1.3968(4) 0.14970(12) 0.0238(6) Uani 1 1 d . . .
O3 O 0.4637(5) 1.1114(5) 0.22411(13) 0.0273(6) Uani 1 1 d . . .
C1 C 0.6402(8) 1.3749(6) 0.08827(19) 0.0235(8) Uani 1 1 d . . .
C2 C 0.8517(7) 1.1797(6) 0.17306(18) 0.0201(8) Uani 1 1 d . . .
H2 H 1.0353 1.1949 0.1894 0.024 Uiso 1 1 calc R . .
C3 C 0.8199(7) 1.0136(6) 0.11278(18) 0.0238(8) Uani 1 1 d . . .
H3 H 0.7120 0.8787 0.1237 0.029 Uiso 1 1 calc R . .
C4 C 0.6910(7) 1.0896(6) 0.22723(18) 0.0212(8) Uani 1 1 d . . .
C5 C 0.6394(7) 0.8080(7) 0.3319(2) 0.0244(8) Uani 1 1 d . . .
C6 C 0.5293(8) 0.6053(7) 0.3054(2) 0.0284(9) Uani 1 1 d . . .
H6 H 0.5773 0.5465 0.2645 0.034 Uiso 1 1 calc R . .
C7 C 0.3482(8) 0.4915(6) 0.34007(19) 0.0274(9) Uani 1 1 d . . .
H7 H 0.2698 0.3555 0.3220 0.033 Uiso 1 1 calc R . .
C8 C 0.2802(7) 0.5713(7) 0.39984(19) 0.0260(9) Uani 1 1 d . . .
C9 C 0.3914(8) 0.7738(7) 0.4254(2) 0.0305(10) Uani 1 1 d . . .
H9 H 0.3449 0.8324 0.4665 0.037 Uiso 1 1 calc R . .
C10 C 0.5709(8) 0.8899(7) 0.3906(2) 0.0295(9) Uani 1 1 d . . .
H10 H 0.6462 1.0280 0.4081 0.035 Uiso 1 1 calc R . .
C11 C 0.0854(7) 0.4400(8) 0.43636(19) 0.0309(9) Uani 1 1 d . . .
H11A H -0.0870 0.4832 0.4189 0.046 Uiso 1 1 calc R . .
H11B H 0.1069 0.4778 0.4834 0.046 Uiso 1 1 calc R . .
H11C H 0.1100 0.2738 0.4304 0.046 Uiso 1 1 calc R . .
C12 C 1.0686(8) 0.9295(12) 0.0895(3) 0.0612(17) Uani 1 1 d . . .
H12A H 1.0348 0.8150 0.0545 0.092 Uiso 1 1 calc R . .
H12B H 1.1707 0.8588 0.1264 0.092 Uiso 1 1 calc R . .
H12C H 1.1625 1.0600 0.0724 0.092 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
C4 S1 C5 100.14(18) . . ?
C1 N1 C3 113.8(3) . . ?
C1 N1 H1A 123.1 . . ?
C3 N1 H1A 123.1 . . ?
C1 O2 C2 110.5(3) . . ?
O1 C1 N1 128.7(4) . . ?
O1 C1 O2 121.5(3) . . ?
N1 C1 O2 109.9(3) . . ?
O2 C2 C4 109.0(3) . . ?
O2 C2 C3 105.3(3) . . ?
C4 C2 C3 108.9(3) . . ?
O2 C2 H2 111.1 . . ?
C4 C2 H2 111.1 . . ?
C3 C2 H2 111.1 . . ?
N1 C3 C12 113.5(4) . . ?
N1 C3 C2 100.2(3) . . ?
C12 C3 C2 113.8(3) . . ?
N1 C3 H3 109.7 . . ?
C12 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
O3 C4 C2 121.8(3) . . ?
O3 C4 S1 126.8(3) . . ?
C2 C4 S1 111.3(3) . . ?
C10 C5 C6 120.3(4) . . ?
C10 C5 S1 121.5(3) . . ?
C6 C5 S1 118.2(3) . . ?
C7 C6 C5 118.6(4) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C6 121.5(4) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 C11 119.7(4) . . ?
C9 C8 C11 121.3(4) . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C5 C10 C9 120.8(4) . . ?
C5 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 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 C4 1.759(4) . ?
S1 C5 1.779(4) . ?
N1 C1 1.342(5) . ?
N1 C3 1.445(5) . ?
N1 H1A 0.8800 . ?
O1 C1 1.217(5) . ?
O2 C1 1.343(5) . ?
O2 C2 1.435(4) . ?
O3 C4 1.197(4) . ?
C2 C4 1.529(5) . ?
C2 C3 1.559(5) . ?
C2 H2 1.0000 . ?
C3 C12 1.502(5) . ?
C3 H3 1.0000 . ?
C5 C10 1.358(5) . ?
C5 C6 1.400(6) . ?
C6 C7 1.392(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(6) . ?
C8 C11 1.513(5) . ?
C9 C10 1.393(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188721
2 PubChem 15288407
