data_2013294
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o250
_journal_page_last  o253
_publ_section_title
;
1,3-Thiazolidine derivatives from regioselective [2+3]-cycloadditions of
azomethine ylides with thioketones
;
loop_
_publ_author_name
  'Domaga\/la, Ma\/lgorzata'
  'Linden, Anthony'
  'Olszak, Tomasz A.'
  'Mlosto\'n, Grzegorz'
  'Heimgartner, Heinz'
_chemical_formula_moiety  'C31 H25 N O4 S'
_chemical_formula_sum  'C31 H25 N O4 S'
_chemical_formula_iupac  'C31 H25 N O4 S'
_chemical_formula_weight  507.58
_chemical_melting_point  476.0(10)
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.8170(10)
_cell_length_b  11.233(2)
_cell_length_c  12.459(2)
_cell_angle_alpha  102.530(10)
_cell_angle_beta  97.910(10)
_cell_angle_gamma  98.520(10)
_cell_volume  1305.7(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.291
_exptl_crystal_density_meas  1.249
_diffrn_ambient_temperature  293(2)
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  S1 0.47266(2) 0.15786(2) 0.27421(2) 0.04390(8) Uani d . 1 . . S
  C2 0.43433(9) 0.27966(9) 0.20390(7) 0.03812(18) Uani d . 1 . . C
  C21 0.43466(11) 0.22312(9) 0.08031(8) 0.0447(2) Uani d . 1 . . C
  O22 0.56275(8) 0.20262(8) 0.06906(6) 0.05527(19) Uani d . 1 . . O
  C23 0.58258(18) 0.14639(16) -0.04158(12) 0.0823(4) Uani d . 1 . . C
  H231 0.6764 0.1309 -0.0389 0.123 Uiso calc R 1 . . H
  H232 0.5671 0.2013 -0.0894 0.123 Uiso calc R 1 . . H
  H233 0.5175 0.0695 -0.0703 0.123 Uiso calc R 1 . . H
  O24 0.33602(9) 0.19505(9) 0.00628(7) 0.0668(2) Uani d . 1 . . O
  C25 0.54619(10) 0.39882(9) 0.25092(8) 0.0429(2) Uani d . 1 . . C
  O26 0.57617(10) 0.45153(7) 0.16975(7) 0.0635(2) Uani d . 1 . . O
  C27 0.6732(2) 0.56893(15) 0.20392(16) 0.1058(7) Uani d . 1 . . C
  H271 0.6409 0.6246 0.2608 0.159 Uiso calc R 1 . . H
  H272 0.6788 0.6043 0.1408 0.159 Uiso calc R 1 . . H
  H273 0.7640 0.5556 0.2328 0.159 Uiso calc R 1 . . H
  O28 0.58971(8) 0.44182(8) 0.34843(7) 0.0580(2) Uani d . 1 . . O
  N3 0.29697(8) 0.30504(7) 0.22731(6) 0.03793(16) Uani d . 1 . . N
  C31 0.26510(10) 0.42140(9) 0.20902(9) 0.0439(2) Uani d . 1 . . C
  C32 0.27735(11) 0.52530(10) 0.29679(10) 0.0521(2) Uani d . 1 . . C
  H321 0.3105 0.5221 0.3695 0.062 Uiso calc R 1 . . H
  C33 0.23992(14) 0.63407(12) 0.27560(13) 0.0665(3) Uani d . 1 . . C
  H331 0.2463 0.7027 0.3346 0.080 Uiso calc R 1 . . H
  C34 0.19394(17) 0.64059(15) 0.16895(15) 0.0824(5) Uani d . 1 . . C
  H341 0.1707 0.7138 0.1552 0.099 Uiso calc R 1 . . H
  C35 0.1821(2) 0.53782(18) 0.08133(15) 0.0924(5) Uani d . 1 . . C
  H351 0.1519 0.5428 0.0086 0.111 Uiso calc R 1 . . H
  C36 0.21478(15) 0.42719(14) 0.10103(11) 0.0677(3) Uani d . 1 . . C
  H361 0.2030 0.3575 0.0421 0.081 Uiso calc R 1 . . H
  C4 0.27737(9) 0.28160(8) 0.33645(7) 0.03611(17) Uani d . 1 . . C
  H41 0.3463 0.3420 0.3948 0.043 Uiso calc R 1 . . H
  C41 0.13248(9) 0.29317(8) 0.36124(8) 0.03849(18) Uani d . 1 . . C
  C42 0.11811(11) 0.33714(10) 0.47121(9) 0.0468(2) Uani d . 1 . . C
  H421 0.1969 0.3596 0.5272 0.056 Uiso calc R 1 . . H
  C43 -0.01254(13) 0.34800(11) 0.49874(11) 0.0585(3) Uani d . 1 . . C
  H431 -0.0210 0.3769 0.5729 0.070 Uiso calc R 1 . . H
  C44 -0.12940(12) 0.31609(12) 0.41651(12) 0.0603(3) Uani d . 1 . . C
  H441 -0.2169 0.3236 0.4349 0.072 Uiso calc R 1 . . H
  C45 -0.11651(11) 0.27319(12) 0.30760(11) 0.0591(3) Uani d . 1 . . C
  H451 -0.1957 0.2516 0.2521 0.071 Uiso calc R 1 . . H
  C46 0.01367(10) 0.26157(10) 0.27909(9) 0.0490(2) Uani d . 1 . . C
  H461 0.0212 0.2325 0.2047 0.059 Uiso calc R 1 . . H
  C5 0.31191(9) 0.15025(8) 0.33236(7) 0.03803(18) Uani d . 1 . . C
  C51 0.33326(10) 0.12451(9) 0.44774(8) 0.04175(19) Uani d . 1 . . C
  C52 0.43511(12) 0.18285(12) 0.53906(9) 0.0553(3) Uani d . 1 . . C
  H521 0.5058 0.2459 0.5350 0.066 Uiso calc R 1 . . H
  C53 0.42914(15) 0.14456(14) 0.63821(10) 0.0660(3) Uani d . 1 . . C
  H531 0.4980 0.1815 0.7006 0.079 Uiso calc R 1 . . H
  C54 0.32346(15) 0.05361(13) 0.64464(10) 0.0648(3) Uani d . 1 . . C
  H541 0.3201 0.0315 0.7121 0.078 Uiso calc R 1 . . H
  C55 0.22128(13) -0.00618(11) 0.55273(10) 0.0576(3) Uani d . 1 . . C
  H551 0.1502 -0.0683 0.5577 0.069 Uiso calc R 1 . . H
  C56 0.22739(11) 0.02863(9) 0.45315(8) 0.0444(2) Uani d . 1 . . C
  C57 0.13980(10) -0.01955(9) 0.34247(9) 0.0437(2) Uani d . 1 . . C
  C58 0.02203(12) -0.11279(10) 0.30486(11) 0.0559(3) Uani d . 1 . . C
  H581 -0.0144 -0.1555 0.3537 0.067 Uiso calc R 1 . . H
  C59 -0.03979(12) -0.14080(11) 0.19411(11) 0.0601(3) Uani d . 1 . . C
  H591 -0.1207 -0.2008 0.1687 0.072 Uiso calc R 1 . . H
  C60 0.01684(12) -0.08088(11) 0.12014(10) 0.0571(3) Uani d . 1 . . C
  H601 -0.0241 -0.1035 0.0450 0.069 Uiso calc R 1 . . H
  C61 0.13470(11) 0.01311(10) 0.15679(9) 0.0477(2) Uani d . 1 . . C
  H611 0.1728 0.0533 0.1070 0.057 Uiso calc R 1 . . H
  C62 0.19344(10) 0.04506(8) 0.26857(8) 0.04010(19) Uani d . 1 . . C
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  S1 0.03917(12) 0.04737(14) 0.05093(14) 0.01507(9) 0.01164(9) 0.01707(10)
  C2 0.0356(4) 0.0407(4) 0.0386(4) 0.0073(3) 0.0087(3) 0.0092(3)
  C21 0.0479(5) 0.0439(5) 0.0419(5) 0.0062(4) 0.0113(4) 0.0088(4)
  O22 0.0544(4) 0.0618(5) 0.0504(4) 0.0144(4) 0.0214(3) 0.0050(3)
  C23 0.1013(11) 0.0899(10) 0.0622(8) 0.0268(9) 0.0455(8) 0.0066(7)
  O24 0.0627(5) 0.0847(6) 0.0433(4) 0.0098(4) 0.0007(4) 0.0028(4)
  C25 0.0364(4) 0.0439(5) 0.0485(5) 0.0078(4) 0.0120(4) 0.0082(4)
  O26 0.0785(6) 0.0480(4) 0.0615(5) -0.0063(4) 0.0252(4) 0.0119(4)
  C27 0.1428(16) 0.0568(8) 0.1052(13) -0.0311(9) 0.0529(12) 0.0070(8)
  O28 0.0505(4) 0.0599(5) 0.0528(4) 0.0002(3) 0.0004(3) 0.0029(4)
  N3 0.0355(3) 0.0421(4) 0.0404(4) 0.0107(3) 0.0095(3) 0.0146(3)
  C31 0.0388(4) 0.0480(5) 0.0538(5) 0.0137(4) 0.0143(4) 0.0237(4)
  C32 0.0502(5) 0.0447(5) 0.0669(7) 0.0122(4) 0.0158(5) 0.0196(5)
  C33 0.0649(7) 0.0506(6) 0.1009(10) 0.0222(5) 0.0368(7) 0.0323(6)
  C34 0.0895(10) 0.0796(9) 0.1174(13) 0.0507(8) 0.0524(9) 0.0623(10)
  C35 0.1108(13) 0.1153(13) 0.0874(11) 0.0623(11) 0.0307(9) 0.0653(11)
  C36 0.0813(9) 0.0794(8) 0.0571(7) 0.0365(7) 0.0145(6) 0.0314(6)
  C4 0.0341(4) 0.0374(4) 0.0370(4) 0.0062(3) 0.0064(3) 0.0097(3)
  C41 0.0369(4) 0.0362(4) 0.0454(5) 0.0075(3) 0.0110(3) 0.0133(4)
  C42 0.0476(5) 0.0469(5) 0.0485(5) 0.0094(4) 0.0143(4) 0.0127(4)
  C43 0.0627(7) 0.0582(6) 0.0656(7) 0.0181(5) 0.0337(6) 0.0198(5)
  C44 0.0444(6) 0.0604(7) 0.0877(9) 0.0167(5) 0.0289(6) 0.0271(6)
  C45 0.0379(5) 0.0635(7) 0.0784(8) 0.0107(5) 0.0075(5) 0.0232(6)
  C46 0.0400(5) 0.0551(6) 0.0520(5) 0.0103(4) 0.0062(4) 0.0133(5)
  C5 0.0370(4) 0.0397(4) 0.0390(4) 0.0084(3) 0.0065(3) 0.0123(3)
  C51 0.0445(5) 0.0443(5) 0.0405(4) 0.0139(4) 0.0077(4) 0.0146(4)
  C52 0.0554(6) 0.0646(7) 0.0454(5) 0.0095(5) 0.0008(5) 0.0182(5)
  C53 0.0718(8) 0.0851(9) 0.0434(6) 0.0231(7) 0.0002(5) 0.0209(6)
  C54 0.0833(9) 0.0776(8) 0.0500(6) 0.0329(7) 0.0190(6) 0.0337(6)
  C55 0.0710(7) 0.0568(6) 0.0586(6) 0.0212(5) 0.0225(6) 0.0296(5)
  C56 0.0506(5) 0.0424(5) 0.0471(5) 0.0166(4) 0.0135(4) 0.0170(4)
  C57 0.0458(5) 0.0371(4) 0.0514(5) 0.0113(4) 0.0115(4) 0.0134(4)
  C58 0.0537(6) 0.0437(5) 0.0736(7) 0.0051(4) 0.0184(5) 0.0196(5)
  C59 0.0497(6) 0.0456(6) 0.0772(8) -0.0020(4) 0.0021(5) 0.0117(5)
  C60 0.0552(6) 0.0475(6) 0.0599(6) 0.0043(5) -0.0048(5) 0.0072(5)
  C61 0.0483(5) 0.0452(5) 0.0472(5) 0.0059(4) 0.0028(4) 0.0114(4)
  C62 0.0393(4) 0.0370(4) 0.0449(5) 0.0084(3) 0.0069(4) 0.0112(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  S1 C2 . 1.8338(10) yes
  S1 C5 . 1.8232(9) yes
  C2 N3 . 1.4734(11) yes
  C2 C21 . 1.5336(13) no
  C2 C25 . 1.5453(13) no
  C21 O24 . 1.1938(13) no
  C21 O22 . 1.3321(12) no
  O22 C23 . 1.4385(14) no
  C23 H231 . 0.9600 no
  C23 H232 . 0.9600 no
  C23 H233 . 0.9600 no
  C25 O28 . 1.1972(12) no
  C25 O26 . 1.3229(13) no
  O26 C27 . 1.4492(16) no
  C27 H271 . 0.9600 no
  C27 H272 . 0.9600 no
  C27 H273 . 0.9600 no
  N3 C31 . 1.4454(12) no
  N3 C4 . 1.4722(11) yes
  C31 C36 . 1.3868(16) no
  C31 C32 . 1.3931(16) no
  C32 C33 . 1.3942(15) no
  C32 H321 . 0.9300 no
  C33 C34 . 1.364(2) no
  C33 H331 . 0.9300 no
  C34 C35 . 1.384(3) no
  C34 H341 . 0.9300 no
  C35 C36 . 1.392(2) no
  C35 H351 . 0.9300 no
  C36 H361 . 0.9300 no
  C4 C41 . 1.5145(12) no
  C4 C5 . 1.5540(13) yes
  C4 H41 . 0.9800 no
  C41 C46 . 1.3875(13) no
  C41 C42 . 1.3860(14) no
  C42 C43 . 1.3882(15) no
  C42 H421 . 0.9300 no
  C43 C44 . 1.3746(19) no
  C43 H431 . 0.9300 no
  C44 C45 . 1.3679(19) no
  C44 H441 . 0.9300 no
  C45 C46 . 1.3895(15) no
  C45 H451 . 0.9300 no
  C46 H461 . 0.9300 no
  C5 C51 . 1.5196(13) no
  C5 C62 . 1.5203(13) no
  C51 C52 . 1.3759(14) no
  C51 C56 . 1.4013(14) no
  C52 C53 . 1.3991(16) no
  C52 H521 . 0.9300 no
  C53 C54 . 1.368(2) no
  C53 H531 . 0.9300 no
  C54 C55 . 1.3853(18) no
  C54 H541 . 0.9300 no
  C55 C56 . 1.3856(14) no
  C55 H551 . 0.9300 no
  C56 C57 . 1.4649(14) no
  C57 C58 . 1.3901(15) no
  C57 C62 . 1.4006(14) no
  C58 C59 . 1.3769(17) no
  C58 H581 . 0.9300 no
  C59 C60 . 1.3823(18) no
  C59 H591 . 0.9300 no
  C60 C61 . 1.3948(15) no
  C60 H601 . 0.9300 no
  C61 C62 . 1.3790(14) no
  C61 H611 . 0.9300 no