#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/37/2003739.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_2003739
loop_
_publ_author_name
'Singh, S. K.'
'Kumar, N.'
'Kumar, A.'
'Bisht, K. S.'
'Parmar, V. S.'
'Errington, W.'
_publ_section_title
;
 (Z)-Ethyl 2-Cyano-3-methylsulfinyl-3-methylthiopropenoate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1630
_journal_page_last               1632
_journal_paper_doi               10.1107/S0108270195002538
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C8 H11 N O3 S2'
_chemical_formula_weight         233.30
_chemical_name_systematic
;
 Z-ethyl 2-cyano-3-methylsulfinyl-3-methylthio propenoate
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.57(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.502(5)
_cell_length_b                   7.036(7)
_cell_length_c                   27.688(24)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      9
_cell_volume                     1069.8(17)
_computing_cell_refinement       'Siemens P3R3 System'
_computing_data_collection       'Siemens P3R3 System'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1991)'
_computing_molecular_graphics    SHELXTL-Plus
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    SHELXTL-Plus
_diffrn_ambient_temperature      220(2)
_diffrn_measurement_device       'Siemens P3R3'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            2460
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.031
_refine_ls_goodness_of_fit_obs   1.057
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_restrained_S_obs      1.057
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_obs          0.0398
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;calc w = 1/[s^2^(Fo^2^) + ( 0.0479P)^2^ + 0.7312P]
where P = (Fo^2^ + 2Fc^2^)/3
;
_refine_ls_wR_factor_all         0.1062
_refine_ls_wR_factor_obs         0.0937
_reflns_number_observed          1486
_reflns_number_total             1900
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ab1239.cif
_cod_data_source_block           seedel
_cod_original_cell_volume        1069.8(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2003739
_cod_database_fobs_code          2003739
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_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
S(1) 1 0.00409(12) 0.18199(11) 0.36020(2) 0.0374(2) Uani d . S
S(2) 1 0.16891(13) 0.46726(11) 0.29436(3) 0.0417(2) Uani d . S
O(1) 1 -0.1942(3) 0.2219(3) 0.32289(8) 0.0517(6) Uani d . O
O(2) 1 0.3436(4) 0.1360(3) 0.43134(7) 0.0544(6) Uani d . O
O(3) 1 0.6294(4) 0.3431(3) 0.45711(7) 0.0452(5) Uani d . O
N(1) 1 0.6811(5) 0.7037(4) 0.38181(10) 0.0564(7) Uani d . N
C(1) 1 0.1667(5) -0.0146(4) 0.33650(11) 0.0434(7) Uani d . C
H(1A) 1 0.0722(5) -0.1300(4) 0.33927(11) 0.065 Uiso d R H
H(1B) 1 0.3222(5) -0.0286(4) 0.35465(11) 0.065 Uiso d R H
H(1C) 1 0.1937(5) 0.0088(4) 0.30273(11) 0.065 Uiso d R H
C(2) 1 0.4489(5) 0.5728(5) 0.27759(10) 0.0459(7) Uani d . C
H(2A) 1 0.4752(5) 0.6919(5) 0.29476(10) 0.069 Uiso d R H
H(2B) 1 0.4396(5) 0.5964(5) 0.24301(10) 0.069 Uiso d R H
H(2C) 1 0.5831(5) 0.4871(5) 0.28591(10) 0.069 Uiso d R H
C(3) 1 0.2348(4) 0.3636(4) 0.34973(9) 0.0307(6) Uani d . C
C(4) 1 0.4138(4) 0.4052(4) 0.38386(9) 0.0313(6) Uani d . C
C(5) 1 0.5666(5) 0.5693(4) 0.38189(9) 0.0383(7) Uani d . C
C(6) 1 0.4553(5) 0.2796(4) 0.42614(9) 0.0364(6) Uani d . C
C(7) 1 0.6812(6) 0.2176(5) 0.49853(11) 0.0604(10) Uani d . C
H(7A) 1 0.5444(6) 0.2194(5) 0.51956(11) 0.072 Uiso d R H
H(7B) 1 0.7030(6) 0.0869(5) 0.48736(11) 0.072 Uiso d R H
C(8) 1 0.9026(6) 0.2827(6) 0.52545(13) 0.0671(11) Uani d . C
H(8A) 1 0.9399(6) 0.2025(6) 0.55343(13) 0.101 Uiso d R H
H(8B) 1 0.8772(6) 0.4123(6) 0.53601(13) 0.101 Uiso d R H
H(8C) 1 1.0371(6) 0.2793(6) 0.50443(13) 0.101 Uiso d R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.0016
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.0000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.0033
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.0060
S S 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1246 0.1234
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O(1) S(1) C(1) 104.68(14) ?
O(1) S(1) C(3) 104.14(13) ?
C(1) S(1) C(3) 96.51(15) ?
C(3) S(2) C(2) 105.65(14) ?
C(6) O(3) C(7) 113.8(2) ?
C(4) C(3) S(2) 129.5(2) y
C(4) C(3) S(1) 121.3(2) y
S(2) C(3) S(1) 109.10(14) y
C(3) C(4) C(5) 123.5(2) y
C(3) C(4) C(6) 119.7(2) y
C(5) C(4) C(6) 116.9(2) y
N(1) C(5) C(4) 176.8(3) ?
O(2) C(6) O(3) 124.3(2) ?
O(2) C(6) C(4) 123.2(2) ?
O(3) C(6) C(4) 112.5(2) ?
O(3) C(7) C(8) 109.0(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) O(1) 1.482(2) y
S(1) C(1) 1.794(3) y
S(1) C(3) 1.837(3) y
S(2) C(3) 1.716(3) y
S(2) C(2) 1.797(3) y
O(2) C(6) 1.196(3) y
O(3) C(6) 1.323(3) y
O(3) C(7) 1.461(4) y
N(1) C(5) 1.137(4) y
C(3) C(4) 1.354(4) y
C(4) C(5) 1.431(4) y
C(4) C(6) 1.473(4) y
C(7) C(8) 1.462(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21187258
