data_2008244
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  411
_journal_page_last  413
_publ_section_title
;
Troglitazone, an euglycemic antidiabetic drug
;
loop_
_publ_author_name
  'K. Vyas'
  'A. Sivalakshmidevi'
  'C. Prabhakar'
  'G. Om Reddy'
_chemical_name_common  'Troglitazone'
_chemical_formula_moiety  'C24 H27 N O5 S'
_chemical_formula_sum  'C24 H27 N O5 S'
_chemical_formula_weight  441.54
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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'
_cell_length_a  16.239(3)
_cell_length_b  11.717(3)
_cell_length_c  11.627(4)
_cell_angle_alpha  90
_cell_angle_beta  93.69(2)
_cell_angle_gamma  90
_cell_volume  2207.7(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  298.2
_exptl_crystal_density_diffrn  1.328
_diffrn_ambient_temperature  298.2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
  S1 0.36107(6) 0.18596(8) 1.22104(8) 0.0706(3) Uani d ? . 1.000
  O1 -0.4051(2) 0.0683(2) 0.4869(2) 0.0699(8) Uani d ? . 1.000
  O2 -0.11140(10)
  0.1371(2) 0.7384(2) 0.0496(6) Uani d ? . 1.000
  O3 0.04710(10)
  0.1868(2) 0.8354(2) 0.0581(6) Uani d ? . 1.000
  O4 0.5073(2) -0.0536(2) 1.1376(2) 0.0930(10)
  Uani d ? . 1.000
  O5 0.4451(2) 0.1892(2) 1.4233(2) 0.0742(8) Uani d ? . 1.000
  N1 0.4831(2) 0.0580(3) 1.2906(2) 0.0592(9) Uani d ? . 1.000
  C1 -0.0957(2) 0.2389(3) 0.8060(2) 0.0488(9) Uani d ? . 1.000
  C2 -0.1715(2) 0.2667(4) 0.8711(3) 0.0610(10)
  Uani d ? . 1.000
  C3 -0.2463(2) 0.2866(3) 0.7895(3) 0.0590(10)
  Uani d ? . 1.000
  C4 -0.2542(2) 0.1954(3) 0.6973(2) 0.0444(8) Uani d ? . 1.000
  C5 -0.3279(2) 0.1777(3) 0.6320(2) 0.0484(8) Uani d ? . 1.000
  C6 -0.3330(2) 0.0895(3) 0.5537(2) 0.0482(8) Uani d ? . 1.000
  C7 -0.2673(2) 0.0159(3) 0.5376(2) 0.0461(8) Uani d ? . 1.000
  C8 -0.1925(2) 0.0357(2) 0.6007(2) 0.0417(8) Uani d ? . 1.000
  C9 -0.1874(2) 0.1259(2) 0.6788(2) 0.0399(7) Uani d ? . 1.000
  C10 -0.4021(2) 0.2545(4) 0.6479(4) 0.0740(10)
  Uani d ? . 1.000
  C11 -0.2780(3) -0.0799(4) 0.4524(4) 0.0710(10)
  Uani d ? . 1.000
  C12 -0.1174(2) -0.0371(4) 0.5851(4) 0.0640(10)
  Uani d ? . 1.000
  C13 -0.0720(3) 0.3349(4) 0.7270(4) 0.0710(10)
  Uani d ? . 1.000
  C14 -0.0266(2) 0.2057(3) 0.8926(3) 0.0550(10)
  Uani d ? . 1.000
  C15 0.1139(2) 0.1445(3) 0.9002(2) 0.0490(8) Uani d ? . 1.000
  C16 0.1863(2) 0.1347(3) 0.8440(3) 0.0580(10)
  Uani d ? . 1.000
  C17 0.2556(2) 0.0899(3) 0.9008(3) 0.0610(10)
  Uani d ? . 1.000
  C18 0.2563(2) 0.0539(3) 1.0140(3) 0.0550(10)
  Uani d ? . 1.000
  C19 0.1845(2) 0.0682(3) 1.0685(3) 0.0650(10)
  Uani d ? . 1.000
  C20 0.1138(2) 0.1123(3) 1.0142(3) 0.0620(10)
  Uani d ? . 1.000
  C21 0.3307(2) -0.0008(3) 1.0759(4) 0.0650(10)
  Uani d ? . 1.000
  C22 0.3966(2) 0.0840(3) 1.1178(3) 0.0570(10)
  Uani d ? . 1.000
  C23 0.4685(2) 0.0204(3) 1.1802(3) 0.0630(10)
  Uani d ? . 1.000
  C24 0.4358(2) 0.1457(3) 1.3293(3) 0.0570(10)
  Uani d ? . 1.000
  H1 -0.443(3) 0.106(4) 0.492(4) 0.13(2) Uiso d ? . 1.000
  H2 0.530(2) 0.033(3) 1.340(3) 0.080(10)
  Uiso d ? . 1.000
  H3 -0.183(2) 0.199(3) 0.922(3) 0.060(10)
  Uiso d ? . 1.000
  H4 -0.161(2) 0.333(3) 0.924(3) 0.070(10)
  Uiso d ? . 1.000
  H5 -0.297(2) 0.285(3) 0.836(3) 0.070(10)
  Uiso d ? . 1.000
  H6 -0.244(2) 0.361(3) 0.757(3) 0.060(10)
  Uiso d ? . 1.000
  H7 -0.385(3) 0.320(4) 0.686(4) 0.14(2) Uiso d ? . 1.000
  H8 -0.440(3) 0.210(4) 0.688(4) 0.13(2) Uiso d ? . 1.000
  H9 -0.429(2) 0.272(3) 0.572(4) 0.110(10)
  Uiso d ? . 1.000
  H10 -0.240(3) -0.134(4) 0.464(4) 0.11(2) Uiso d ? . 1.000
  H11 -0.255(3) -0.061(4) 0.384(4) 0.15(2) Uiso d ? . 1.000
  H12 -0.331(3) -0.088(4) 0.422(4) 0.15(2) Uiso d ? . 1.000
  H13 -0.114(2) -0.062(4) 0.502(4) 0.120(10)
  Uiso d ? . 1.000
  H14 -0.114(3) -0.090(4) 0.632(4) 0.13(2) Uiso d ? . 1.000
  H15 -0.068(3) 0.008(4) 0.601(4) 0.13(2) Uiso d ? . 1.000
  H16 -0.021(2) 0.311(3) 0.691(3) 0.090(10)
  Uiso d ? . 1.000
  H17 -0.115(2) 0.352(3) 0.666(3) 0.070(10)
  Uiso d ? . 1.000
  H18 -0.061(2) 0.397(3) 0.771(3) 0.090(10)
  Uiso d ? . 1.000
  H19 -0.043(2) 0.135(3) 0.934(2) 0.055(9) Uiso d ? . 1.000
  H20 -0.016(2) 0.268(3) 0.954(3) 0.070(10)
  Uiso d ? . 1.000
  H21 0.186(2) 0.161(3) 0.765(3) 0.070(10)
  Uiso d ? . 1.000
  H22 0.304(2) 0.085(3) 0.863(3) 0.070(10)
  Uiso d ? . 1.000
  H23 0.184(2) 0.044(3) 1.146(3) 0.070(10)
  Uiso d ? . 1.000
  H24 0.066(2) 0.116(3) 1.051(3) 0.070(10)
  Uiso d ? . 1.000
  H25 0.359(2) -0.052(3) 1.023(3) 0.090(10)
  Uiso d ? . 1.000
  H26 0.314(2) -0.042(3) 1.149(3) 0.080(10)
  Uiso d ? . 1.000
  H27 0.408(2) 0.120(3) 1.043(3) 0.100(10)
  Uiso d ? . 1.000
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 0.0716(6) 0.0663(6) 0.0710(5) 0.0225(5) -0.0169(4) -0.0084(5)
  O1 0.0520(10)
  0.090(2) 0.0650(10)
  -0.0020(10)
  -0.0190(10)
  -0.0030(10)
  O2 0.0390(10)
  0.0570(10)
  0.0520(10)
  0.0063(9) -0.0036(8) -0.0130(10)
  O3 0.0450(10)
  0.085(2) 0.0440(10)
  -0.0030(10)
  0.0005(9) 0.0030(10)
  O4 0.095(2) 0.106(2) 0.078(2) 0.050(2) 0.003(2) -0.004(2)
  O5 0.090(2) 0.069(2) 0.0620(10)
  -0.0020(10)
  -0.0120(10)
  -0.0060(10)
  N1 0.050(2) 0.070(2) 0.056(2) 0.0060(10)
  -0.0040(10)
  0.0110(10)
  C1 0.046(2) 0.057(2) 0.044(2) -0.0040(10)
  0.0020(10)
  -0.0110(10)
  C2 0.053(2) 0.072(2) 0.057(2) 0.001(2) 0.003(2) -0.024(2)
  C3 0.052(2) 0.058(2) 0.066(2) 0.008(2) 0.008(2) -0.016(2)
  C4 0.043(2) 0.047(2) 0.0440(10)
  0.0030(10)
  0.0050(10)
  -0.0010(10)
  C5 0.0390(10)
  0.056(2) 0.051(2) 0.0080(10)
  0.0030(10)
  0.0060(10)
  C6 0.042(2) 0.061(2) 0.041(2) -0.0050(10)
  -0.0020(10)
  0.0110(10)
  C7 0.056(2) 0.047(2) 0.0350(10)
  -0.0070(10)
  0.0020(10)
  0.0020(10)
  C8 0.045(2) 0.042(2) 0.0380(10)
  0.0030(10)
  0.0040(10)
  0.0040(10)
  C9 0.0380(10)
  0.046(2) 0.0360(10)
  0.0020(10)
  0.0010(10)
  0.0020(10)
  C10 0.047(2) 0.081(3) 0.092(3) 0.021(2) -0.001(2) -0.003(3)
  C11 0.074(3) 0.074(3) 0.065(2) -0.001(2) -0.006(2) -0.023(2)
  C12 0.063(2) 0.059(2) 0.068(2) 0.018(2) 0.002(2) -0.013(2)
  C13 0.060(2) 0.075(3) 0.077(3) -0.008(2) -0.003(2) 0.010(2)
  C14 0.046(2) 0.072(2) 0.047(2) -0.008(2) 0.0000(10)
  -0.004(2)
  C15 0.046(2) 0.057(2) 0.043(2) -0.0070(10)
  -0.0030(10)
  -0.0030(10)
  C16 0.054(2) 0.078(2) 0.042(2) -0.001(2) 0.0030(10)
  0.000(2)
  C17 0.050(2) 0.077(2) 0.056(2) 0.000(2) 0.007(2) -0.007(2)
  C18 0.053(2) 0.058(2) 0.053(2) -0.003(2) -0.0040(10)
  -0.001(2)
  C19 0.060(2) 0.088(3) 0.048(2) -0.003(2) 0.000(2) 0.013(2)
  C20 0.049(2) 0.088(3) 0.051(2) -0.004(2) 0.009(2) 0.006(2)
  C21 0.062(2) 0.059(2) 0.072(2) 0.004(2) -0.006(2) -0.001(2)
  C22 0.055(2) 0.063(2) 0.054(2) 0.006(2) -0.0010(10)
  0.006(2)
  C23 0.056(2) 0.070(2) 0.062(2) 0.010(2) 0.002(2) 0.009(2)
  C24 0.053(2) 0.059(2) 0.057(2) -0.010(2) -0.0030(10)
  0.010(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  S1 C22 . . 1.814(4) yes
  S1 C24 . . 1.756(3) yes
  O1 C6 . . 1.384(3) n
  O1 H1 . . 0.76(4) no
  O2 C1 . . 1.442(3) n
  O2 C9 . . 1.381(3) n
  O3 C14 . . 1.424(4) n
  O3 C15 . . 1.372(3) n
  O4 C23 . . 1.198(4) yes
  O5 C24 . . 1.206(4) yes
  N1 C23 . . 1.362(4) yes
  N1 C24 . . 1.376(4) yes
  N1 H2 . . 0.97(3) no
  C1 C2 . . 1.521(4) n
  C1 C13 . . 1.517(5) n
  C1 C14 . . 1.510(4) n
  C2 C3 . . 1.511(5) n
  C2 H3 . . 1.02(3) no
  C2 H4 . . 1.00(3) no
  C3 C4 . . 1.513(4) n
  C3 H5 . . 1.02(3) no
  C3 H6 . . 0.95(3) no
  C4 C5 . . 1.390(4) n
  C4 C9 . . 1.384(4) n
  C5 C6 . . 1.376(4) n
  C5 C10 . . 1.525(4) n
  C6 C7 . . 1.394(4) n
  C7 C8 . . 1.397(4) n
  C7 C11 . . 1.500(5) n
  C8 C9 . . 1.393(4) n
  C8 C12 . . 1.509(4) n
  C10 H7 . . 0.92(5) no
  C10 H8 . . 0.96(5) no
  C10 H9 . . 0.99(4) no
  C11 H10 . . 0.89(4) no
  C11 H11 . . 0.92(5) no
  C11 H12 . . 0.92(5) no
  C12 H13 . . 1.02(4) no
  C12 H14 . . 0.83(5) no
  C12 H15 . . 0.96(5) no
  C13 H16 . . 0.98(4) no
  C13 H17 . . 0.99(3) no
  C13 H18 . . 0.90(4) no
  C14 H19 . . 1.00(3) no
  C14 H20 . . 1.03(3) no
  C15 C16 . . 1.385(4) n
  C15 C20 . . 1.378(4) n
  C16 C17 . . 1.373(4) n
  C16 H21 . . 0.97(3) no
  C17 C18 . . 1.380(4) n
  C17 H22 . . 0.93(3) no
  C18 C19 . . 1.373(4) n
  C18 C21 . . 1.509(4) n
  C19 C20 . . 1.375(4) n
  C19 H23 . . 0.94(3) no
  C20 H24 . . 0.92(3) no
  C21 C22 . . 1.517(5) n
  C21 H25 . . 0.99(4) no
  C21 H26 . . 1.03(3) no
  C22 C23 . . 1.528(4) n
  C22 H27 . . 1.00(4) no