#------------------------------------------------------------------------------
#$Date: 2018-01-26 10:40:08 +0200 (Fri, 26 Jan 2018) $
#$Revision: 205727 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242347.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_2242347
loop_
_publ_author_name
'Boukhedena, Wafia'
'Fiala, Abdelali'
'Brahim Ladouani, Hayet'
'Lemallem, Salah Eddine'
'Hamdouni, Noudjoud'
'Boudjada, Ali'
_publ_section_title
;
 Crystal structure of ethyl 2-cyano-2-(1,3-dithian-2-ylidene)acetate
;
_journal_coeditor_code           SU5404
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              65
_journal_page_last               68
_journal_paper_doi               10.1107/S2056989017017893
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C9 H11 N O2 S2'
_chemical_formula_moiety         'C9 H11 N O2 S2'
_chemical_formula_sum            'C9 H11 N O2 S2'
_chemical_formula_weight         229.31
_chemical_name_systematic
;
Ethyl 2-cyano-2-(1,3-dithian-2-ylidene)acetate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 111.830(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.826(3)
_cell_length_b                   8.0772(6)
_cell_length_c                   18.431(2)
_cell_measurement_reflns_used    1541
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.88
_cell_measurement_theta_min      3.72
_cell_volume                     2187.1(6)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1994)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.02
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4539
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.391
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.344
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0673P)²+0.4223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                1667
_reflns_number_total             2132
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5404sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2187.1(5)
_cod_database_code               2242347
_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, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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_occupancy
S S2 0.12671(5) 0.08363(8) 0.29431(4) 0.0555(3) Uani d 1
S S1 0.11241(5) 0.40461(8) 0.37170(4) 0.0589(3) Uani d 1
O O1 0.14349(14) -0.1692(2) 0.40827(11) 0.0641(5) Uani d 1
O O2 0.12483(13) -0.1107(2) 0.52062(11) 0.0592(5) Uani d 1
N N1 0.1307(2) 0.2907(3) 0.55919(14) 0.0741(7) Uani d 1
C C1 0.13376(16) -0.0706(3) 0.45311(14) 0.0477(6) Uani d 1
C C2 0.13016(16) 0.1100(3) 0.44342(13) 0.0447(6) Uani d 1
C C3 0.13080(18) 0.2096(3) 0.50818(15) 0.0512(6) Uani d 1
C C4 0.12494(15) 0.1895(3) 0.37572(14) 0.0449(6) Uani d 1
C C5 0.1624(2) 0.4577(4) 0.30133(16) 0.0620(7) Uani d 1
H H5A 0.166410 0.577323 0.299200 0.074 Uiso calc 1
H H5B 0.224000 0.414405 0.319553 0.074 Uiso calc 1
C C6 0.1113(2) 0.3938(3) 0.21943(16) 0.0639(7) Uani d 1
H H6A 0.153558 0.381976 0.192819 0.077 Uiso calc 1
H H6B 0.065809 0.474754 0.190915 0.077 Uiso calc 1
C C7 0.06477(19) 0.2289(3) 0.21774(15) 0.0615(7) Uani d 1
H H7A 0.053615 0.176859 0.167585 0.074 Uiso calc 1
H H7B 0.006049 0.249883 0.221227 0.074 Uiso calc 1
C C8 0.1298(2) -0.2859(3) 0.54028(17) 0.0617(7) Uani d 1
H H8A 0.185483 -0.334042 0.539292 0.074 Uiso calc 1
H H8B 0.078396 -0.344992 0.503306 0.074 Uiso calc 1
C C9 0.1279(2) -0.2958(4) 0.62053(19) 0.0731(9) Uani d 1
H H9A 0.131070 -0.409675 0.636284 0.110 Uiso calc 1
H H9B 0.179046 -0.236653 0.656364 0.110 Uiso calc 1
H H9C 0.072531 -0.247544 0.620570 0.110 Uiso calc 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'
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
C4 S2 C7 100.12(13)
C4 S1 C5 101.16(13)
C1 O2 C8 116.8(2)
O1 C1 O2 124.3(2)
O1 C1 C2 125.9(2)
O2 C1 C2 109.8(2)
C4 C2 C3 118.1(2)
C4 C2 C1 124.0(2)
C3 C2 C1 117.9(2)
N1 C3 C2 179.1(3)
C2 C4 S2 122.55(18)
C2 C4 S1 117.99(18)
S2 C4 S1 119.43(14)
C6 C5 S1 114.9(2)
C6 C5 H5A 108.5
S1 C5 H5A 108.5
C6 C5 H5B 108.5
S1 C5 H5B 108.5
H5A C5 H5B 107.5
C5 C6 C7 113.3(2)
C5 C6 H6A 108.9
C7 C6 H6A 108.9
C5 C6 H6B 108.9
C7 C6 H6B 108.9
H6A C6 H6B 107.7
C6 C7 S2 115.69(19)
C6 C7 H7A 108.4
S2 C7 H7A 108.4
C6 C7 H7B 108.4
S2 C7 H7B 108.4
H7A C7 H7B 107.4
O2 C8 C9 106.2(2)
O2 C8 H8A 110.5
C9 C8 H8A 110.5
O2 C8 H8B 110.5
C9 C8 H8B 110.5
H8A C8 H8B 108.7
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 C4 1.736(2)
S2 C7 1.817(3)
S1 C4 1.747(2)
S1 C5 1.805(3)
O1 C1 1.198(3)
O2 C1 1.343(3)
O2 C8 1.456(3)
N1 C3 1.146(3)
C1 C2 1.469(3)
C2 C4 1.378(3)
C2 C3 1.436(3)
C5 C6 1.514(4)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.517(4)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.492(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 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
C8 O2 C1 O1 1.6(4)
C8 O2 C1 C2 -178.2(2)
O1 C1 C2 C4 9.4(4)
O2 C1 C2 C4 -170.8(2)
O1 C1 C2 C3 -171.5(2)
O2 C1 C2 C3 8.2(3)
C3 C2 C4 S2 178.22(18)
C1 C2 C4 S2 -2.7(3)
C3 C2 C4 S1 -3.9(3)
C1 C2 C4 S1 175.18(18)
C7 S2 C4 C2 153.6(2)
C7 S2 C4 S1 -24.31(17)
C5 S1 C4 C2 153.59(19)
C5 S1 C4 S2 -28.43(18)
C4 S1 C5 C6 65.6(2)
S1 C5 C6 C7 -32.9(3)
C5 C6 C7 S2 -37.1(3)
C4 S2 C7 C6 65.9(2)
C1 O2 C8 C9 174.2(2)

_cod_database_fobs_code 2242347
