#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/17/7151755.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_7151755
loop_
_publ_author_name
'Kissane, Marie'
'Murphy, Maureen'
'O'Brien, Elisabeth'
'Chopra, Jay'
'Murphy, Linda'
'Collins, Stuart G.'
'Lawrence, Simon E.'
'Maguire, Anita R.'
_publ_section_title
;
 Addition-substitution reactions of 2-thio-3-chloroacrylamides with
 carbon, nitrogen, oxygen, sulfur and selenium nucleophiles.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2452
_journal_page_last               2472
_journal_paper_doi               10.1039/c0ob00805b
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C14 H18 N2 O4 S'
_chemical_formula_sum            'C14 H18 N2 O4 S'
_chemical_formula_weight         310.36
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.20(3)
_cell_angle_beta                 83.98(4)
_cell_angle_gamma                80.88(4)
_cell_formula_units_Z            2
_cell_length_a                   5.6949(16)
_cell_length_b                   9.6545(13)
_cell_length_c                   13.611(2)
_cell_measurement_reflns_used    2813
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.3
_cell_volume                     706.0(3)
_computing_cell_refinement       '(CrystalClear; Rigaku, 2004)'
_computing_data_collection       '(CrystalClear; Rigaku, 2004)'
_computing_data_reduction        '(CrystalClear; Rigaku, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97; PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type
'Rigaku Saturn 724, partial X goniometer, ACTOR SM robot'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6184
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9522
_exptl_absorpt_correction_T_min  0.9522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2004)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0683
_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)+(0.0706P)²+1.6596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1817
_reflns_number_gt                2176
_reflns_number_total             2509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00805b.txt
_cod_data_source_block           compound_24a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        706.0(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151755
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.12093(17) -0.00669(10) 0.32647(7) 0.0196(3) Uani 1 1 d . . .
O1 O 0.3678(5) 0.0128(3) 0.3258(2) 0.0244(7) Uani 1 1 d . . .
O2 O 0.0190(5) -0.1020(3) 0.41721(19) 0.0232(6) Uani 1 1 d . . .
O3 O -0.1580(5) 0.3479(3) 0.1479(2) 0.0299(7) Uani 1 1 d . . .
O4 O -0.7562(5) 0.5186(3) 0.4020(2) 0.0268(7) Uani 1 1 d . . .
N1 N 0.2322(6) 0.2803(3) 0.1708(2) 0.0224(8) Uani 1 1 d . . .
H1 H 0.3419 0.2227 0.2101 0.027 Uiso 1 1 calc R . .
N2 N -0.3844(6) 0.2925(3) 0.3838(2) 0.0215(7) Uani 1 1 d . . .
C1 C 0.1047(7) -0.0805(4) 0.2228(3) 0.0203(8) Uani 1 1 d . . .
C2 C 0.2839(8) -0.0687(4) 0.1456(3) 0.0261(9) Uani 1 1 d . . .
H2 H 0.4128 -0.0174 0.1459 0.031 Uiso 1 1 calc R . .
C3 C 0.2734(8) -0.1328(5) 0.0674(3) 0.0307(10) Uani 1 1 d . . .
H3 H 0.3970 -0.1259 0.0143 0.037 Uiso 1 1 calc R . .
C4 C 0.0873(8) -0.2055(5) 0.0659(3) 0.0288(10) Uani 1 1 d . . .
H4 H 0.0808 -0.2476 0.0114 0.035 Uiso 1 1 calc R . .
C5 C -0.0919(8) -0.2180(5) 0.1439(3) 0.0319(10) Uani 1 1 d . . .
H5 H -0.2196 -0.2702 0.1434 0.038 Uiso 1 1 calc R . .
C6 C -0.0857(8) -0.1549(5) 0.2223(3) 0.0278(10) Uani 1 1 d . . .
H6 H -0.2095 -0.1621 0.2754 0.033 Uiso 1 1 calc R . .
C7 C 0.0021(7) 0.2713(4) 0.2001(3) 0.0205(8) Uani 1 1 d . . .
C8 C -0.0528(7) 0.1629(4) 0.2984(3) 0.0193(8) Uani 1 1 d . . .
C9 C -0.2377(7) 0.1774(4) 0.3700(3) 0.0199(8) Uani 1 1 d . . .
H9 H -0.2656 0.0880 0.4189 0.024 Uiso 1 1 calc R . .
C10 C -0.3578(8) 0.4464(4) 0.3350(3) 0.0274(10) Uani 1 1 d . . .
H10A H -0.2571 0.4555 0.2702 0.033 Uiso 1 1 calc R . .
H10B H -0.2788 0.4846 0.3813 0.033 Uiso 1 1 calc R . .
C11 C -0.5998(8) 0.5336(5) 0.3128(3) 0.0295(10) Uani 1 1 d . . .
H11A H -0.5813 0.6379 0.2827 0.035 Uiso 1 1 calc R . .
H11B H -0.6707 0.5009 0.2614 0.035 Uiso 1 1 calc R . .
C12 C -0.7854(7) 0.3691(4) 0.4461(3) 0.0249(9) Uani 1 1 d . . .
H12A H -0.8582 0.3341 0.3963 0.030 Uiso 1 1 calc R . .
H12B H -0.8953 0.3598 0.5083 0.030 Uiso 1 1 calc R . .
C13 C -0.5528(7) 0.2755(4) 0.4744(3) 0.0240(9) Uani 1 1 d . . .
H13A H -0.4859 0.3042 0.5288 0.029 Uiso 1 1 calc R . .
H13B H -0.5787 0.1720 0.5018 0.029 Uiso 1 1 calc R . .
C14 C 0.3048(8) 0.3825(5) 0.0760(3) 0.0265(9) Uani 1 1 d . . .
H14A H 0.2737 0.3495 0.0175 0.040 Uiso 1 1 calc R . .
H14B H 0.4754 0.3880 0.0750 0.040 Uiso 1 1 calc R . .
H14C H 0.2145 0.4792 0.0713 0.040 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
O2 S1 O1 117.78(17) . . ?
O2 S1 C8 109.39(18) . . ?
O1 S1 C8 109.20(18) . . ?
O2 S1 C1 107.34(17) . . ?
O1 S1 C1 105.75(18) . . ?
C8 S1 C1 106.79(18) . . ?
C11 O4 C12 109.8(3) . . ?
C7 N1 C14 121.6(3) . . ?
C9 N2 C10 126.5(3) . . ?
C9 N2 C13 119.7(3) . . ?
C10 N2 C13 111.5(3) . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 S1 120.0(3) . . ?
C6 C1 S1 119.3(3) . . ?
C1 C2 C3 119.2(4) . . ?
C4 C3 C2 120.7(4) . . ?
C3 C4 C5 120.0(4) . . ?
C6 C5 C4 120.3(4) . . ?
C5 C6 C1 119.1(4) . . ?
O3 C7 N1 122.0(4) . . ?
O3 C7 C8 120.8(4) . . ?
N1 C7 C8 117.2(3) . . ?
C9 C8 C7 127.3(3) . . ?
C9 C8 S1 114.5(3) . . ?
C7 C8 S1 118.1(3) . . ?
N2 C9 C8 132.3(4) . . ?
N2 C10 C11 109.5(3) . . ?
O4 C11 C10 112.4(3) . . ?
O4 C12 C13 111.9(3) . . ?
N2 C13 C12 109.9(3) . . ?
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 O2 1.439(3) . ?
S1 O1 1.446(3) . ?
S1 C8 1.735(4) . ?
S1 C1 1.771(4) . ?
O3 C7 1.226(5) . ?
O4 C11 1.415(5) . ?
O4 C12 1.423(5) . ?
N1 C7 1.338(5) . ?
N1 C14 1.445(5) . ?
N2 C9 1.327(5) . ?
N2 C10 1.467(5) . ?
N2 C13 1.467(5) . ?
C1 C2 1.379(6) . ?
C1 C6 1.394(6) . ?
C2 C3 1.387(6) . ?
C3 C4 1.366(6) . ?
C4 C5 1.387(6) . ?
C5 C6 1.379(6) . ?
C7 C8 1.480(5) . ?
C8 C9 1.376(5) . ?
C10 C11 1.507(6) . ?
C12 C13 1.499(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653474
