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#$Date: 2023-01-06 11:59:08 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280219 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106425.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_8106425
loop_
_publ_author_name
'Mabkhot, Yahia N.'
'Ghabbour, Hazem A.'
'Al-aizari, Faiz A.'
'Al-Showiman, Salim'
_publ_section_title
;
 Crystal structure of (Z)-Ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene)
 acetate, C14H14N2O2S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              41
_journal_page_last               42
_journal_paper_doi               10.1515/ncrs-2016-0121
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C14 H14 N2 O2 S'
_chemical_formula_weight         274.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                91.054(2)
_cell_angle_beta                 109.380(2)
_cell_angle_gamma                113.769(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6471(4)
_cell_length_b                   9.5576(5)
_cell_length_c                   9.7098(5)
_cell_measurement_reflns_used    9193
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.23
_cell_measurement_theta_min      2.26
_cell_volume                     681.95(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19934
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.259
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.241
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0608
_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)+(0.0741P)²+0.5848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1745
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2345
_reflns_number_total             3119
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2016-0121_suppl.cif
_cod_data_source_block           a_a
_cod_database_code               8106425
_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.
;
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.945
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.57896(10) 0.36123(8) 0.14783(8) 0.0524(3) Uani 1 1 d . . . . .
O1 O 0.2177(3) 0.2648(3) 0.0047(3) 0.0708(7) Uani 1 1 d . . . . .
O2 O 0.0428(3) 0.3411(3) 0.0835(3) 0.0779(8) Uani 1 1 d . . . . .
N1 N 0.6838(3) 0.6103(2) 0.3276(2) 0.0391(5) Uani 1 1 d . . . . .
N2 N 0.2674(4) 0.6137(3) 0.3722(3) 0.0662(8) Uani 1 1 d . . . . .
C1 C 0.7642(5) 0.7946(4) 0.5420(3) 0.0672(9) Uani 1 1 d . . . . .
H1A H 0.8039 0.7305 0.6041 0.081 Uiso 1 1 calc R U . . .
C2 C 0.7753(7) 0.9313(5) 0.6024(5) 0.0902(13) Uani 1 1 d . . . . .
H2A H 0.8224 0.9611 0.7071 0.108 Uiso 1 1 calc R U . . .
C3 C 0.7203(5) 1.0241(4) 0.5149(5) 0.0750(11) Uani 1 1 d . . . . .
H3A H 0.7259 1.1169 0.5582 0.090 Uiso 1 1 calc R U . . .
C4 C 0.6564(5) 0.9837(4) 0.3639(5) 0.0703(9) Uani 1 1 d . . . . .
H4A H 0.6196 1.0496 0.3026 0.084 Uiso 1 1 calc R U . . .
C5 C 0.6449(4) 0.8474(3) 0.3000(3) 0.0541(7) Uani 1 1 d . . . . .
H5A H 0.6032 0.8204 0.1952 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6945(3) 0.7523(3) 0.3900(3) 0.0387(5) Uani 1 1 d . . . . .
C7 C 0.8553(4) 0.6050(4) 0.3404(4) 0.0622(8) Uani 1 1 d . . . . .
H7A H 0.9201 0.6852 0.2909 0.075 Uiso 1 1 calc R U . . .
H7B H 0.9346 0.6257 0.4462 0.075 Uiso 1 1 calc R U . . .
C8 C 0.8136(5) 0.4511(5) 0.2705(5) 0.0839(12) Uani 1 1 d . . . . .
H8A H 0.8357 0.3872 0.3472 0.101 Uiso 1 1 calc R U . . .
H8B H 0.8928 0.4600 0.2141 0.101 Uiso 1 1 calc R U . . .
C9 C 0.5325(3) 0.4940(3) 0.2338(3) 0.0344(5) Uani 1 1 d . . . . .
C10 C 0.3550(3) 0.4713(3) 0.2064(3) 0.0381(5) Uani 1 1 d . . . . .
C11 C 0.2045(4) 0.3489(3) 0.0895(3) 0.0503(7) Uani 1 1 d . . . . .
C12 C -0.1216(5) 0.2288(6) -0.0327(4) 0.0952(14) Uani 1 1 d . . . . .
H12A H -0.2047 0.2772 -0.0753 0.114 Uiso 1 1 calc R U . . .
H12B H -0.0904 0.1956 -0.1129 0.114 Uiso 1 1 calc R U . . .
C13 C -0.2075(8) 0.1007(5) 0.0242(6) 0.1189(19) Uani 1 1 d . . . . .
H13A H -0.3290 0.0353 -0.0493 0.178 Uiso 1 1 calc R U . . .
H13B H -0.2184 0.1354 0.1147 0.178 Uiso 1 1 calc R U . . .
H13C H -0.1359 0.0408 0.0475 0.178 Uiso 1 1 calc R U . . .
C14 C 0.3118(3) 0.5551(3) 0.2986(3) 0.0441(6) Uani 1 1 d . . . . .
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
C9 S1 C8 91.34(13) . .
C11 O2 C12 118.4(3) . .
C9 N1 C6 125.1(2) . .
C9 N1 C7 115.9(2) . .
C6 N1 C7 117.5(2) . .
C2 C1 C6 118.8(3) . .
C2 C1 H1A 120.6 . .
C6 C1 H1A 120.6 . .
C3 C2 C1 121.1(3) . .
C3 C2 H2A 119.5 . .
C1 C2 H2A 119.5 . .
C2 C3 C4 119.7(3) . .
C2 C3 H3A 120.1 . .
C4 C3 H3A 120.1 . .
C3 C4 C5 120.5(3) . .
C3 C4 H4A 119.8 . .
C5 C4 H4A 119.8 . .
C6 C5 C4 118.9(3) . .
C6 C5 H5A 120.6 . .
C4 C5 H5A 120.6 . .
C5 C6 C1 120.9(3) . .
C5 C6 N1 120.4(2) . .
C1 C6 N1 118.7(2) . .
C8 C7 N1 108.5(2) . .
C8 C7 H7A 110.0 . .
N1 C7 H7A 110.0 . .
C8 C7 H7B 110.0 . .
N1 C7 H7B 110.0 . .
H7A C7 H7B 108.4 . .
C7 C8 S1 108.5(2) . .
C7 C8 H8A 110.0 . .
S1 C8 H8A 110.0 . .
C7 C8 H8B 110.0 . .
S1 C8 H8B 110.0 . .
H8A C8 H8B 108.4 . .
N1 C9 C10 126.5(2) . .
N1 C9 S1 112.08(17) . .
C10 C9 S1 121.42(18) . .
C9 C10 C14 122.3(2) . .
C9 C10 C11 120.2(2) . .
C14 C10 C11 117.3(2) . .
O1 C11 O2 122.9(3) . .
O1 C11 C10 125.5(3) . .
O2 C11 C10 111.6(2) . .
C13 C12 O2 110.1(4) . .
C13 C12 H12A 109.6 . .
O2 C12 H12A 109.6 . .
C13 C12 H12B 109.6 . .
O2 C12 H12B 109.6 . .
H12A C12 H12B 108.1 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
N2 C14 C10 175.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C9 1.750(2) .
S1 C8 1.796(4) .
O1 C11 1.204(3) .
O2 C11 1.351(4) .
O2 C12 1.452(4) .
N1 C9 1.332(3) .
N1 C6 1.431(3) .
N1 C7 1.468(3) .
N2 C14 1.146(3) .
C1 C2 1.376(5) .
C1 C6 1.377(4) .
C1 H1A 0.9500 .
C2 C3 1.355(6) .
C2 H2A 0.9500 .
C3 C4 1.368(5) .
C3 H3A 0.9500 .
C4 C5 1.385(4) .
C4 H4A 0.9500 .
C5 C6 1.367(4) .
C5 H5A 0.9500 .
C7 C8 1.458(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.390(3) .
C10 C14 1.421(3) .
C10 C11 1.447(4) .
C12 C13 1.386(6) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.4(7) . . . .
C1 C2 C3 C4 -1.6(7) . . . .
C2 C3 C4 C5 1.1(6) . . . .
C3 C4 C5 C6 1.5(5) . . . .
C4 C5 C6 C1 -3.5(4) . . . .
C4 C5 C6 N1 179.8(3) . . . .
C2 C1 C6 C5 3.0(5) . . . .
C2 C1 C6 N1 179.8(3) . . . .
C9 N1 C6 C5 -59.4(3) . . . .
C7 N1 C6 C5 106.2(3) . . . .
C9 N1 C6 C1 123.8(3) . . . .
C7 N1 C6 C1 -70.5(4) . . . .
C9 N1 C7 C8 -13.1(4) . . . .
C6 N1 C7 C8 179.9(3) . . . .
N1 C7 C8 S1 19.4(4) . . . .
C9 S1 C8 C7 -17.0(3) . . . .
C6 N1 C9 C10 -16.3(4) . . . .
C7 N1 C9 C10 177.9(3) . . . .
C6 N1 C9 S1 165.93(19) . . . .
C7 N1 C9 S1 0.0(3) . . . .
C8 S1 C9 N1 10.0(2) . . . .
C8 S1 C9 C10 -167.9(3) . . . .
N1 C9 C10 C14 -12.8(4) . . . .
S1 C9 C10 C14 164.8(2) . . . .
N1 C9 C10 C11 173.2(2) . . . .
S1 C9 C10 C11 -9.2(4) . . . .
C12 O2 C11 O1 -1.5(5) . . . .
C12 O2 C11 C10 177.2(3) . . . .
C9 C10 C11 O1 -3.6(5) . . . .
C14 C10 C11 O1 -177.9(3) . . . .
C9 C10 C11 O2 177.7(2) . . . .
C14 C10 C11 O2 3.4(4) . . . .
C11 O2 C12 C13 102.0(5) . . . .
