#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/49/2214973.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214973
loop_
_publ_author_name
'Abbasi, Alireza'
'Kianmehr, Ebrahim'
'Beheshti, Saeideh'
'Eriksson, Lars'
_publ_section_title
;
 Dimethyl 2-chloro-3-tosylmaleate
;
_journal_coeditor_code           BH2129
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3774
_journal_page_last               o3774
_journal_paper_doi               10.1107/S1600536807039128
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H13 Cl O6 S'
_chemical_formula_moiety         'C13 H13 Cl O6 S'
_chemical_formula_sum            'C13 H13 Cl O6 S'
_chemical_formula_weight         332.74
_chemical_name_systematic
;
Dimethyl 2-chloro-3-tosylmaleate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Manual editing of the cif file from SHELXL-97'
_cell_angle_alpha                90.00
_cell_angle_beta                 100.879(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4167(14)
_cell_length_b                   12.9964(13)
_cell_length_c                   9.5511(10)
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      32.1
_cell_measurement_theta_min      3.8
_cell_volume                     1513.6(3)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 12
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Oxford Diffraction X-calibur2 with a Sapphire-3 CCD detector'
_diffrn_measurement_method       'ω scans at different φ'
_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  0.0702
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9792
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.81
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  0.9297
_exptl_absorpt_correction_T_min  0.8146
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.303
_refine_ls_extinction_coef       0.040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0446
_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)+(0.0868P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                2475
_reflns_number_total             3298
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2129.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214973
_cod_database_fobs_code          2214973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.29026(4) 0.12068(4) 0.04566(5) 0.03976(17) Uani d . 1
Cl Cl1 0.14986(4) 0.12677(4) 0.30129(5) 0.04899(19) Uani d . 1
O O1 0.23422(11) 0.21700(10) 0.04155(14) 0.0519(4) Uani d . 1
O O2 0.32811(12) 0.08590(13) -0.07918(14) 0.0561(4) Uani d . 1
O O3 0.14474(11) -0.06627(11) -0.13420(14) 0.0503(4) Uani d . 1
O O4 0.26860(14) -0.14406(13) 0.03464(18) 0.0694(5) Uani d . 1
O O5 0.03110(11) -0.05397(11) 0.33034(14) 0.0511(4) Uani d . 1
O O6 0.03986(14) -0.12829(11) 0.12083(17) 0.0615(4) Uani d . 1
C C1 0.20074(14) 0.01944(13) 0.08335(18) 0.0362(4) Uani d . 1
C C2 0.14118(14) 0.02430(13) 0.18619(18) 0.0364(4) Uani d . 1
C C3 0.06504(14) -0.06168(14) 0.2081(2) 0.0414(4) Uani d . 1
C C4 -0.0495(2) -0.1296(2) 0.3566(3) 0.0689(7) Uani d . 1
H H4A -0.1066 -0.1351 0.2738 0.103 Uiso calc R 1
H H4B -0.0805 -0.1082 0.4366 0.103 Uiso calc R 1
H H4C -0.0145 -0.1952 0.3766 0.103 Uiso calc R 1
C C5 0.20747(15) -0.07510(15) -0.0063(2) 0.0433(4) Uani d . 1
C C6 0.1592(2) -0.1451(2) -0.2352(3) 0.0730(7) Uani d . 1
H H6A 0.2359 -0.1536 -0.2356 0.109 Uiso calc R 1
H H6B 0.1217 -0.1255 -0.3286 0.109 Uiso calc R 1
H H6C 0.1295 -0.2088 -0.2085 0.109 Uiso calc R 1
C C7 0.40081(14) 0.11797(14) 0.19050(19) 0.0388(4) Uani d . 1
C C8 0.47378(16) 0.03585(16) 0.2040(2) 0.0505(5) Uani d . 1
H H8 0.4648 -0.0168 0.1368 0.061 Uiso calc R 1
C C9 0.56025(17) 0.03382(18) 0.3196(3) 0.0576(6) Uani d . 1
H H9 0.6094 -0.0209 0.3293 0.069 Uiso calc R 1
C C10 0.57497(16) 0.11112(17) 0.4204(2) 0.0513(5) Uani d . 1
C C11 0.50243(18) 0.19318(18) 0.4025(2) 0.0567(5) Uani d . 1
H H11 0.5128 0.2467 0.4683 0.068 Uiso calc R 1
C C12 0.41541(16) 0.19742(16) 0.2894(2) 0.0492(5) Uani d . 1
H H12 0.3671 0.2528 0.2794 0.059 Uiso calc R 1
C C13 0.6695(2) 0.1068(2) 0.5454(3) 0.0758(8) Uani d . 1
H H13A 0.6709 0.0407 0.5905 0.114 Uiso calc R 1
H H13B 0.6607 0.1595 0.6127 0.114 Uiso calc R 1
H H13C 0.7371 0.1175 0.5125 0.114 Uiso calc R 1
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'
Cl Cl 0.1484 0.1585 '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
O1 S1 O2 119.16(9)
O1 S1 C7 110.09(9)
O2 S1 C7 108.57(9)
O1 S1 C1 109.24(8)
O2 S1 C1 104.31(9)
C7 S1 C1 104.36(8)
C5 O3 C6 115.46(18)
C3 O5 C4 116.47(17)
C2 C1 C5 123.54(16)
C2 C1 S1 124.02(14)
C5 C1 S1 112.27(13)
C1 C2 C3 121.07(16)
C1 C2 Cl1 122.01(14)
C3 C2 Cl1 116.91(13)
O6 C3 O5 125.76(17)
O6 C3 C2 121.84(17)
O5 C3 C2 112.40(16)
O5 C4 H4A 109.5
O5 C4 H4B 109.5
H4A C4 H4B 109.5
O5 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O4 C5 O3 126.52(19)
O4 C5 C1 121.76(18)
O3 C5 C1 111.53(16)
O3 C6 H6A 109.5
O3 C6 H6B 109.5
H6A C6 H6B 109.5
O3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C12 C7 C8 120.58(18)
C12 C7 S1 120.23(15)
C8 C7 S1 119.19(15)
C9 C8 C7 118.79(19)
C9 C8 H8 120.6
C7 C8 H8 120.6
C10 C9 C8 121.5(2)
C10 C9 H9 119.3
C8 C9 H9 119.3
C9 C10 C11 118.47(19)
C9 C10 C13 120.4(2)
C11 C10 C13 121.1(2)
C12 C11 C10 121.6(2)
C12 C11 H11 119.2
C10 C11 H11 119.2
C11 C12 C7 119.09(19)
C11 C12 H12 120.5
C7 C12 H12 120.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 1.4291(14) n
S1 O2 1.4348(15) n
S1 C7 1.7557(19) n
S1 C1 1.8020(18) n
Cl1 C2 1.7172(18) y
O3 C5 1.324(2) n
O3 C6 1.442(3) n
O4 C5 1.192(2) n
O5 C3 1.318(2) n
O5 C4 1.457(2) n
O6 C3 1.201(2) n
C1 C2 1.338(2) y
C1 C5 1.509(3) ?
C2 C3 1.504(2) ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
C7 C12 1.388(3) ?
C7 C8 1.390(3) ?
C8 C9 1.387(3) ?
C8 H8 0.9300 ?
C9 C10 1.380(3) ?
C9 H9 0.9300 ?
C10 C11 1.385(3) ?
C10 C13 1.509(3) ?
C11 C12 1.377(3) ?
C11 H11 0.9300 ?
C12 H12 0.9300 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
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_publ_flag
O1 S1 C1 C2 -46.44(17) ?
O2 S1 C1 C2 -174.88(15) ?
C7 S1 C1 C2 71.26(16) ?
O1 S1 C1 C5 138.23(12) ?
O2 S1 C1 C5 9.79(15) ?
C7 S1 C1 C5 -104.07(13) ?
C5 C1 C2 C3 -7.4(3) y
S1 C1 C2 C3 177.75(12) y
C5 C1 C2 Cl1 171.16(14) y
S1 C1 C2 Cl1 -3.7(2) y
C4 O5 C3 O6 -4.2(3) ?
C4 O5 C3 C2 175.59(17) ?
C1 C2 C3 O6 -13.4(3) ?
Cl1 C2 C3 O6 167.92(16) ?
C1 C2 C3 O5 166.77(16) ?
Cl1 C2 C3 O5 -11.9(2) ?
C6 O3 C5 O4 -4.8(3) ?
C6 O3 C5 C1 170.36(18) ?
C2 C1 C5 O4 -82.7(3) ?
S1 C1 C5 O4 92.7(2) ?
C2 C1 C5 O3 101.9(2) ?
S1 C1 C5 O3 -82.72(16) ?
O1 S1 C7 C12 6.95(18) ?
O2 S1 C7 C12 139.03(16) ?
C1 S1 C7 C12 -110.17(16) ?
O1 S1 C7 C8 -172.52(15) ?
O2 S1 C7 C8 -40.44(18) ?
C1 S1 C7 C8 70.36(17) ?
C12 C7 C8 C9 1.2(3) ?
S1 C7 C8 C9 -179.35(16) ?
C7 C8 C9 C10 0.0(3) ?
C8 C9 C10 C11 -1.5(3) ?
C8 C9 C10 C13 179.8(2) ?
C9 C10 C11 C12 1.8(3) ?
C13 C10 C11 C12 -179.5(2) ?
C10 C11 C12 C7 -0.6(3) ?
C8 C7 C12 C11 -0.9(3) ?
S1 C7 C12 C11 179.65(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21184469
2 PubChem 139072865
