#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008376.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_2008376
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  656
_journal_page_last  659
_publ_section_title
;
Two novel optically-active penam derivatives
;
loop_
_publ_author_name
  'Danilovski, Aleksandar'
  'Vinkovi\'c, Mladen'
  'Herak, Jure J.'
_chemical_formula_moiety  'C15 H16 N2 O S'
_chemical_formula_sum  'C15 H16 N2 O S'
_chemical_formula_weight  272.36
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,y+1/2,-z'
_cell_length_a  5.295(6)
_cell_length_b  11.559(8)
_cell_length_c  11.698(11)
_cell_angle_alpha  90.00
_cell_angle_beta  90.64(8)
_cell_angle_gamma  90.00
_cell_volume  715.9(12)
_cell_formula_units_Z  2
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.263
_diffrn_ambient_temperature  293
_refine_ls_R_factor_obs  0.061
_refine_ls_wR_factor_obs  0.115
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_refinement_flags
_atom_site_type_symbol
  N1 -0.1436(8) -0.6238(4) -0.7943(4) 0.0572(12) Uij ? ? N
  C2 0.0221(9) -0.5614(5) -0.7210(4) 0.0494(13) Uij ? ? C
  C21 0.1548(12) -0.4682(5) -0.7565(5) 0.061(2) Uij ? ? C
  C22 0.120(2) -0.4258(7) -0.8781(5) 0.090(2) Uij ? ? C
  C23 0.3451(17) -0.4040(7) -0.6875(6) 0.084(2) Uij ? ? c
  C3 0.0316(9) -0.6179(5) -0.6071(4) 0.0500(13) Uij ? ? C
  N31 0.1808(9) -0.5902(4) -0.5274(4) 0.0581(12) Uij ? ? N
  C32 0.1818(12) -0.6557(5) -0.4210(4) 0.066(2) Uij ? ? C
  C33 0.3571(10) -0.6043(5) -0.3319(4) 0.0557(14) Uij ? ? C
  C34 0.3368(12) -0.6383(6) -0.2174(4) 0.062(2) Uij ? ? C
  C35 0.5045(13) -0.5980(6) -0.1369(5) 0.071(2) Uij ? ? C
  C36 0.6924(13) -0.5222(7) -0.1658(6) 0.082(2) Uij ? ? C
  C37 0.7126(12) -0.4868(7) -0.2782(6) 0.075(2) Uij ? ? C
  C38 0.5485(11) -0.5278(6) -0.3590(5) 0.063(2) Uij ? ? C
  S4 -0.1839(3) -0.73824(14) -0.60190(11) 0.0670(5) Uij ? ? S
  C5 -0.3223(10) -0.7024(5) -0.7397(5) 0.065(2) Uij ? ? C
  C6 -0.2829(12) -0.7902(6) -0.8396(5) 0.069(2) Uij ? ? C
  C7 -0.0715(11) -0.7081(5) -0.8746(5) 0.062(2) Uij ? ? C
  O71 0.1029(9) -0.7109(4) -0.9379(3) 0.0835(14) Uij ? ? O
  H5 -0.4945(10) -0.6718(5) -0.7354(5) 0.065 Uiso ? ? H
  H6A -0.2262(12) -0.8663(6) -0.8156(5) 0.122 Uiso ? ? H
  H6B -0.4227(12) -0.7948(6) -0.8937(5) 0.061 Uiso ? ? H
  H32A 0.2333(12) -0.7346(5) -0.4365(4) 0.092 Uiso ? ? H
  H32B 0.0118(12) -0.6579(5) -0.3911(4) 0.092 Uiso ? ? H
  H34 0.2086(12) -0.6885(6) -0.1960(4) 0.076 Uiso ? ? H
  H35 0.4908(13) -0.6224(6) -0.0615(5) 0.048 Uiso ? ? H
  H36 0.8049(13) -0.4949(7) -0.1104(6) 0.065 Uiso ? ? H
  H37 0.8383(12) -0.4349(7) -0.2987(6) 0.060 Uiso ? ? H
  H38 0.5656(11) -0.5039(6) -0.4344(5) 0.073 Uiso ? ? H
  H22A 0.226(2)  -0.3596(7) -0.8903(5) 0.176 Uiso ? ? H
  H22B -0.053(2)  -0.4046(7) -0.8909(5) 0.145 Uiso ? ? H
  H22C 0.166(2)  -0.4862(7) -0.9303(5) 0.194 Uiso ? ? H
  H23A 0.4120(17) -0.3416(7) -0.7321(6) 0.388 Uiso ? ? H
  H23B 0.4796(17) -0.4554(7) -0.6656(6) 0.244 Uiso ? ? H
  H23C 0.2670(17) -0.3734(7) -0.6203(6) 0.235 Uiso ? ? H
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
_atom_site_aniso_type_symbol
  N1 0.064(3) 0.046(3) 0.062(3) 0.002(3) 0.000(2) 0.002(2) N
  C2 0.049(3) 0.043(3) 0.056(3) 0.005(3) -0.006(2) -0.006(3) C
  C21 0.075(4) 0.046(3) 0.062(3) 0.002(3) 0.003(3) -0.005(3) C
  C22 0.136(8) 0.060(4) 0.074(5) -0.005(5) -0.002(4) 0.017(4) C
  C23 0.119(6) 0.059(4) 0.075(5) -0.031(5) -0.001(4) -0.004(4) C
  C3 0.048(3) 0.043(3) 0.060(3) 0.002(3) 0.006(3) -0.007(3) C
  N31 0.066(3) 0.051(3) 0.058(3) -0.003(3) -0.001(2) 0.000(2) N
  C32 0.082(4) 0.051(4) 0.064(3) -0.002(3) -0.003(3) 0.008(3) C
  C33 0.053(3) 0.053(3) 0.061(3) 0.016(3) -0.001(3) -0.002(3) C
  C34 0.075(4) 0.054(3) 0.058(3) 0.013(3) 0.004(3) 0.009(3) C
  C35 0.093(5) 0.070(4) 0.049(3) 0.025(4) -0.010(3) 0.001(3) C
  C36 0.073(4) 0.098(6) 0.075(5) 0.015(5) -0.025(3) -0.029(4) C
  C37 0.061(4) 0.090(5) 0.073(4) -0.013(4) 0.004(3) -0.012(4) C
  C38 0.062(4) 0.071(4) 0.056(4) -0.004(4) 0.006(3) -0.006(3) C
  S4 0.0752(10) 0.0640(9) 0.0619(8) -0.0185(9) 0.0069(6) -0.0002(8) S
  C5 0.051(3) 0.057(4) 0.088(4) -0.002(3) 0.004(3) -0.007(3) C
  C6 0.069(4) 0.070(4) 0.068(4) -0.013(4) -0.012(3) -0.006(3) C
  C7 0.065(4) 0.060(4) 0.062(3) 0.001(3) 0.000(3) -0.013(3) C
  O71 0.102(3) 0.076(3) 0.073(2) -0.018(3) 0.018(2) -0.019(2) O
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
  S4 C3 ? ? 1.801(6) ?
  S4 C5 ? ? 1.811(6) ?
  O71 C7 ? ? 1.190(6) ?
  N1 C7 ? ? 1.409(8) yes
  N1 C2 ? ? 1.417(7) ?
  N1 C5 ? ? 1.464(7) ?
  N31 C3 ? ? 1.257(6) yes
  N31 C32 ? ? 1.457(7) yes
  C3 C2 ? ? 1.484(7) yes
  C2 C21 ? ? 1.354(8) ?
  C5 C6 ? ? 1.563(8) ?
  C6 C7 ? ? 1.527(9) ?
  C32 C33 ? ? 1.510(7) ?
  C33 C38 ? ? 1.384(8) ?
  C33 C34 ? ? 1.402(7) ?
  C34 C35 ? ? 1.369(8) ?
  C35 C36 ? ? 1.371(10) ?
  C36 C37 ? ? 1.383(10) ?
  C37 C38 ? ? 1.361(9) ?
  C21 C23 ? ? 1.483(9) ?
  C21 C22 ? ? 1.513(8) ?