#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005183.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_2005183
loop_
_publ_author_name
'Pom\'es Hern\'andez, R.'
'Duque Rodr\'iguez, J.'
'Novoa de Armas, H.'
'Toscano, R. A.'
_publ_section_title
;
 Ethyl Cyano(4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene)acetate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1731
_journal_page_last               1733
_journal_paper_doi               10.1107/S0108270195017227
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C14 H12 N2 O3 S1'
_chemical_formula_sum            'C14 H12 N2 O3 S'
_chemical_formula_weight         288.32
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 96.65(3)
_cell_angle_gamma                90.
_cell_formula_units_Z            8
_cell_length_a                   9.811(3)
_cell_length_b                   12.845(2)
_cell_length_c                   22.107(3)
_cell_measurement_reflns_used    41
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10.2
_cell_measurement_theta_min      7.8
_cell_volume                     2767.2(10)
_computing_cell_refinement       'SHELXTL-Plus (Sheldrick, 1991)'
_computing_data_collection       'XSCANS (Siemens, 1992)'
_computing_data_reduction        SHELXTL-Plus
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  'SHELXL93 and SHELXTL-Plus'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    SHELXTL-Plus
_diffrn_measurement_device       'Siemens P3/PC'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5183
_diffrn_reflns_theta_max         25.0
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.23
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   semi-empirical
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      1.370
_exptl_crystal_description       laminar
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.12
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4873
_refine_ls_R_factor_obs          0.060
_refine_ls_shift/esd_max         0.048
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
w = 1/[\s^2^(F~o~^2^) + (0.0444P)^2^ + 1.7550P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_obs         0.114
_reflns_number_observed          2176
_reflns_number_total             4875
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            sz1026.cif
_cod_data_source_block           sz1026a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C14 H12 N2 O3 S1'
_cod_database_code               2005183
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,1/2-y,1/2+z
-x,-y,-z
-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
S(1A) .0728(1) .0529(1) .2692(1) .055(1)
O(1A) .0083(5) .0799(3) .0953(2) .094(2)
O(2A) -.0083(4) .1311(3) .3718(2) .073(1)
O(3A) -.1898(5) .2359(4) .3754(2) .097(2)
N(2A) -.3212(5) .3281(3) .2471(2) .060(1)
N(3A) -.0675(4) .1502(3) .1802(2) .043(1)
C(2A) -.0531(5) .1437(3) .2428(2) .040(1)
C(4A) .0096(6) .0808(4) .1492(3) .060(2)
C(5A) .0910(5) .0100(4) .1936(2) .060(2)
C(6A) -.1276(5) .1989(3) .2807(2) .042(1)
C(7A) -.0997(6) .1846(4) .3466(2) .054(1)
C(8A) -.2356(6) .2702(4) .2601(2) .044(1)
C(9A) -.1564(5) .2233(4) .1447(2) .041(1)
C(10A) -.2829(5) .1904(4) .1200(2) .054(1)
C(11A) -.3659(6) .2590(5) .0845(2) .067(2)
C(12A) -.3228(6) .3578(5) .0748(2) .065(2)
C(13A) -.1952(6) .3898(4) .1007(2) .060(2)
C(14A) -.1107(5) .3224(4) .1355(2) .047(1)
C(15A) -.1684(9) .2375(6) .4412(3) .114(3)
C(16A) -.1500(8) .3392(6) .4631(3) .121(3)
S(1B) -.4697(2) .5732(1) .2594(1) .061(1)
O(1B) -.5195(4) .5936(3) .0844(2) .084(1)
O(2B) -.3511(4) .6680(3) .3578(2) .074(1)
O(3B) -.2503(3) .8250(3) .3615(1) .054(1)
N(2B) -.2136(5) .9206(4) .2270(2) .085(2)
N(3B) -.4266(4) .6876(3) .1675(2) .044(1)
C(2B) -.4009(5) .6849(3) .2296(2) .042(1)
C(4B) -.4942(6) .6006(4) .1384(3) .058(2)
C(5B) -.5276(6) .5236(4) .1847(2) .066(2)
C(6B) -.3296(5) .7583(4) .2660(2) .042(1)
C(7B) -.3130(5) .7435(4) .3322(2) .051(1)
C(8B) -.2668(5) .8483(4) .2426(2) .052(1)
C(9B) -.3985(5) .7750(4) .1298(2) .043(1)
C(10B) -.2893(6) .7730(5) .0969(3) .067(2)
C(11B) -.2682(7) .8579(6) .0595(3) .086(2)
C(12B) -.3571(8) .9403(5) .0562(3) .083(2)
C(13B) -.4649(7) .9405(4) .0887(3) .068(2)
C(14B) -.4878(5) .8583(4) .1261(2) .052(1)
C(15B) -.2234(6) .8154(4) .4277(2) .070(2)
C(16B) -.1820(7) .9185(5) .4530(3) .088(2)
H(5AA) .1869(5) .0113(4) .1869(2) .060
H(5AB) .0578(5) -.0609(4) .1880(2) .060
H(10A) -.3128(5) .1232(4) .1270(2) .060
H(11A) -.4520(6) .2375(5) .0669(2) .060
H(12A) -.3794(6) .4035(5) .0509(2) .060
H(13A) -.1662(6) .4576(4) .0946(2) .060
H(14A) -.0240(5) .3434(4) .1526(2) .060
H(15A) -.2469(9) .2066(6) .4573(3) .060
H(15B) -.0881(9) .1963(6) .4553(3) .060
H(16A) -.1361(8) .3382(6) .5068(3) .060
H(16B) -.2300(8) .3798(6) .4497(3) .060
H(16C) -.0714(8) .3695(6) .4478(3) .060
H(5BA) -.4827(6) .4578(4) .1784(2) .060
H(5BB) -.6258(6) .5117(4) .1809(2) .060
H(10B) -.2299(6) .7163(5) .0993(3) .060
H(11B) -.1939(7) .8583(6) .0370(3) .060
H(12B) -.3428(8) .9967(5) .0313(3) .060
H(13B) -.5247(7) .9969(4) .0858(3) .050
H(14B) -.5623(5) .8589(4) .1486(2) .060
H(15C) -.1509(6) .7651(4) .4384(2) .060
H(15D) -.3053(6) .7917(4) .4442(2) .060
H(16D) -.1638(7) .9137(5) .4965(3) .060
H(16E) -.2546(7) .9676(5) .4423(3) .060
H(16F) -.1006(7) .9411(5) .4365(3) .060
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
C(2A) S(1A) C(5A) 92.1(2) yes
C(7A) O(3A) C(15A) 117.6(5) yes
C(2A) N(3A) C(4A) 117.1(4) yes
C(2A) N(3A) C(9A) 124.7(4) yes
C(4A) N(3A) C(9A) 118.2(4) yes
C(6A) C(2A) N(3A) 125.7(4) yes
C(6A) C(2A) S(1A) 123.1(4) yes
N(3A) C(2A) S(1A) 111.2(4) yes
O(1A) C(4A) N(3A) 123.5(5) yes
O(1A) C(4A) C(5A) 126.4(5) yes
N(3A) C(4A) C(5A) 110.0(5) yes
C(4A) C(5A) S(1A) 108.8(4) yes
C(2A) C(6A) C(8A) 124.1(4) yes
C(2B) S(1B) C(5B) 92.2(2) yes
C(9A) C(14A) C(13A) 118.8(5) yes
C(12A) C(11A) C(10A) 120.7(5) yes
O(3B) C(7B) C(6B) 111.8(4) yes
C(16A) C(15A) O(3A) 111.0(6) yes
C(2B) C(6B) C(7B) 119.0(4) yes
C(8B) C(6B) C(7B) 117.5(4) yes
N(2B) C(8B) C(6B) 176.4(5) yes
C(10B) C(9B) N(3B) 120.6(5) yes
C(14B) C(9B) N(3B) 118.4(4) yes
C(11A) C(12A) C(13A) 119.8(5) yes
C(2B) C(6B) C(8B) 123.5(4) yes
C(7B) O(3B) C(15B) 115.9(4) yes
C(2A) C(6A) C(7A) 119.5(5) yes
C(8A) C(6A) C(7A) 116.3(5) yes
O(2A) C(7A) O(3A) 124.2(5) yes
O(2A) C(7A) C(6A) 124.8(5) yes
O(3A) C(7A) C(6A) 111.0(5) yes
N(2A) C(8A) C(6A) 176.0(5) yes
C(10A) C(9A) C(14A) 121.8(5) yes
C(10A) C(9A) N(3A) 118.6(4) yes
C(14A) C(9A) N(3A) 119.6(4) yes
C(9A) C(10A) C(11A) 118.6(5) yes
C(14A) C(13A) C(12A) 120.4(5) yes
O(2B) C(7B) C(6B) 124.7(5) yes
C(10B) C(9B) C(14B) 121.0(5) yes
C(9B) C(10B) C(11B) 118.7(6) yes
C(12B) C(11B) C(10B) 119.9(6) yes
C(2B) N(3B) C(4B) 117.3(4) yes
C(2B) N(3B) C(9B) 125.0(4) yes
C(4B) N(3B) C(9B) 117.5(4) yes
N(3B) C(2B) C(6B) 126.3(4) yes
N(3B) C(2B) S(1B) 111.4(3) yes
C(6B) C(2B) S(1B) 122.3(4) yes
O(1B) C(4B) N(3B) 123.1(5) yes
O(1B) C(4B) C(5B) 127.0(5) yes
N(3B) C(4B) C(5B) 109.9(5) yes
C(4B) C(5B) S(1B) 109.0(4) yes
O(2B) C(7B) O(3B) 123.5(5) yes
C(13B) C(12B) C(11B) 120.6(6) yes
C(12B) C(13B) C(14B) 120.8(6) yes
C(13B) C(14B) C(9B) 119.0(5) yes
O(3B) C(15B) C(16B) 108.2(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1A) C(2A) 1.749(5) yes
S(1A) C(5A) 1.788(5) yes
O(1A) C(4A) 1.191(6) yes
O(2A) C(7A) 1.212(6) yes
O(3A) C(7A) 1.324(6) yes
O(3A) C(15A) 1.445(6) yes
N(2A) C(8A) 1.133(6) yes
N(3A) C(2A) 1.376(5) yes
N(3A) C(4A) 1.400(6) yes
N(3A) C(9A) 1.449(5) yes
C(2A) C(6A) 1.371(6) yes
C(4A) C(5A) 1.499(7) yes
C(6B) C(7B) 1.467(6) yes
C(9B) C(10B) 1.363(7) yes
C(6A) C(8A) 1.435(7) yes
C(6A) C(7A) 1.463(7) yes
C(9A) C(10A) 1.364(6) yes
C(9A) C(14A) 1.373(6) yes
C(10A) C(11A) 1.381(7) yes
C(12B) C(13B) 1.346(8) yes
C(11A) C(12A) 1.362(8) yes
O(2B) C(7B) 1.203(6) yes
O(3B) C(7B) 1.343(5) yes
O(3B) C(15B) 1.461(6) yes
N(2B) C(8B) 1.139(6) yes
N(3B) C(2B) 1.366(6) yes
N(3B) C(4B) 1.416(6) yes
N(3B) C(9B) 1.443(6) yes
C(2B) C(6B) 1.376(6) yes
C(4B) C(5B) 1.487(7) yes
C(6B) C(8B) 1.434(7) yes
C(9B) C(14B) 1.380(6) yes
C(10B) C(11B) 1.397(8) yes
C(11B) C(12B) 1.368(9) yes
C(15B) C(16B) 1.476(7) yes
C(15A) C(16A) 1.398(9) yes
S(1B) C(2B) 1.748(5) yes
S(1B) C(5B) 1.800(5) yes
O(1B) C(4B) 1.195(6) yes
C(13B) C(14B) 1.375(7) yes
C(12A) C(13A) 1.378(7) yes
C(13A) C(14A) 1.372(6) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139055055