#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011172.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_2011172
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  e305
_journal_page_last  e306
_publ_section_title
;
Benzyl
5-{2-[2-(diethoxyphosphinoyl)acetyl]-3-oxo-7-thia-2,4-diazabicyclo[3.3.0]oct-6-
yl}pentanoate, a novel biotin derivative
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_[local]_cod_cif_authors_sg_H-M  'P 21'
_[local]_cod_cif_authors_sg_Hall 'P 2y1'
loop_
_publ_author_name
  'Amspacher, David R.'
  'Blanchard, Carol Z. '
  'Saraiva, Marcelo C. '
  'Waldrop, Grover L. '
  'Strongin, Robert M. '
  'Fronczek, Frank R.'
_chemical_formula_moiety  'C23 H33 N2 O7 P S'
_chemical_formula_sum  'C23 H33 N2 O7 P S'
_chemical_formula_weight  512.57
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  -x,1/2+y,-z
_cell_length_a  10.455(2)
_cell_length_b  12.410(2)
_cell_length_c  10.592(2)
_cell_angle_alpha  90
_cell_angle_beta  115.077(10)
_cell_angle_gamma  90
_cell_volume  1244.7(4)
_cell_formula_units_z  2
_cell_measurement_temperature  100
_exptl_crystal_density_diffrn  1.368
_diffrn_ambient_temperature  100
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
  S  .15464(8)  -.00002(6)  .50200(7)  .02093(16) Uani d . 1 . . S
  P  .56073(8)  -.31423(6)  .84128(7)  .01808(16) Uani d . 1 . . P
  O1  .5366(2)  -.07268(17)  .9157(2)  .0216(4) Uani d . 1 . . O
  O2  .0933(3)  .59257(17)  .9411(2)  .0261(5) Uani d . 1 . . O
  O3  -.0240(2)  .4366(2)  .9121(3)  .0343(6) Uani d . 1 . . O
  O4  .5615(2)  -.16967(16)  .5502(2)  .0216(5) Uani d . 1 . . O
  O5  .6095(2)  -.32900(18)  .99252(19)  .0268(5) Uani d . 1 . . O
  O6  .3987(2)  -.28939(16)  .7593(2)  .0219(5) Uani d . 1 . . O
  O7  .5824(2)  -.41463(16)  .7604(2)  .0218(4) Uani d . 1 . . O
  N1  .4361(3)  .0764(2)  .7816(2)  .0187(5) Uani d . 1 . . N
  H1N  .4262  .1153  .8463  .022 Uiso calc R 1 . . H
  N2  .4998(3)  -.05748(19)  .6824(2)  .0165(5) Uani d . 1 . . N
  C1  .2299(3)  .1324(2)  .5644(3)  .0179(6) Uani d . 1 . . C
  H1  .2099  .1799  .4819  .022 Uiso calc R 1 . . H
  C2  .3903(3)  .1139(2)  .6390(3)  .0175(6) Uani d . 1 . . C
  H2  .4427  .1806  .6363  .021 Uiso calc R 1 . . H
  C3  .4299(3)  .0184(2)  .5662(3)  .0171(6) Uani d . 1 . . C
  H3  .4969  .0429  .5271  .021 Uiso calc R 1 . . H
  C4  .2950(3)  -.0274(2)  .4510(3)  .0206(6) Uani d . 1 . . C
  H4A  .3046  -.1060  .4413  .025 Uiso calc R 1 . . H
  H4B  .2757  .0075  .3607  .025 Uiso calc R 1 . . H
  C5  .4946(3)  -.0219(2)  .8069(3)  .0177(6) Uani d . 1 . . C
  C6  .1605(3)  .1812(2)  .6508(3)  .0184(5) Uani d . 1 . . C
  H6A  .1810  .1347  .7331  .022 Uiso calc R 1 . . H
  H6B  .0569  .1810  .5946  .022 Uiso calc R 1 . . H
  C7  .2068(3)  .2955(2)  .7011(3)  .0188(6) Uani d . 1 . . C
  H7A  .1921  .3426  .6207  .023 Uiso calc R 1 . . H
  H7B  .3085  .2963  .7651  .023 Uiso calc R 1 . . H
  C8  .1212(3)  .3375(2)  .7765(3)  .0192(6) Uani d . 1 . . C
  H8A  .0195  .3317  .7131  .023 Uiso calc R 1 . . H
  H8B  .1393  .2909  .8582  .023 Uiso calc R 1 . . H
  C9  .1536(3)  .4534(2)  .8257(3)  .0180(6) Uani d . 1 . . C
  H9A  .2544  .4595  .8915  .022 Uiso calc R 1 . . H
  H9B  .1368  .5006  .7448  .022 Uiso calc R 1 . . H
  C10  .0640(3)  .4900(3)  .8958(3)  .0206(6) Uani d . 1 . . C
  C11  .0151(4)  .6351(3) 1.0157(3)  .0281(7) Uani d . 1 . . C
  H11A  -.0822  .6060  .9739  .034 Uiso calc R 1 . . H
  H11B  .0091  .7145 1.0062  .034 Uiso calc R 1 . . H
  C12  .0853(3)  .6056(2) 1.1682(3)  .0212(6) Uani d . 1 . . C
  C13  .0476(3)  .5115(3) 1.2166(3)  .0245(6) Uani d . 1 . . C
  H13  -.0217  .4647 1.1529  .029 Uiso calc R 1 . . H
  C14  .1109(3)  .4863(3) 1.3571(3)  .0267(7) Uani d . 1 . . C
  H14  .0850  .4220 1.3892  .032 Uiso calc R 1 . . H
  C15  .2113(3)  .5536(3) 1.4510(3)  .0249(7) Uani d . 1 . . C
  H15  .2543  .5357 1.5473  .030 Uiso calc R 1 . . H
  C16  .2487(4)  .6466(3) 1.4046(3)  .0294(7) Uani d . 1 . . C
  H16  .3173  .6935 1.4689  .035 Uiso calc R 1 . . H
  C17  .1861(3)  .6722(3) 1.2635(3)  .0260(7) Uani d . 1 . . C
  H17  .2130  .7364 1.2321  .031 Uiso calc R 1 . . H
  C18  .5688(3)  -.1469(2)  .6651(3)  .0168(6) Uani d . 1 . . C
  C19  .6567(3)  -.2129(2)  .7933(3)  .0198(6) Uani d . 1 . . C
  H19A  .7020  -.1631  .8730  .024 Uiso calc R 1 . . H
  H19B  .7329  -.2490  .7772  .024 Uiso calc R 1 . . H
  C20  .3089(4)  -.2659(3)  .8308(4)  .0351(9) Uani d . 1 . . C
  H20A  .3432  -.2005  .8890  .042 Uiso calc R 1 . . H
  H20B  .3112  -.3268  .8920  .042 Uiso calc R 1 . . H
  C21  .1624(4)  -.2487(3)  .7230(5)  .0451(11) Uani d . 1 . . C
  H21A  .1617  -.1897  .6612  .068 Uiso calc R 1 . . H
  H21B  .1009  -.2302  .7684  .068 Uiso calc R 1 . . H
  H21C  .1280  -.3147  .6683  .068 Uiso calc R 1 . . H
  C22  .5271(3)  -.5193(2)  .7756(3)  .0252(7) Uani d . 1 . . C
  H22A  .4858  -.5564  .6843  .030 Uiso calc R 1 . . H
  H22B  .4514  -.5091  .8073  .030 Uiso calc R 1 . . H
  C23  .6414(4)  -.5870(3)  .8784(4)  .0296(7) Uani d . 1 . . C
  H23A  .7192  -.5930  .8502  .044 Uiso calc R 1 . . H
  H23B  .6044  -.6590  .8818  .044 Uiso calc R 1 . . H
  H23C  .6760  -.5536  .9708  .044 Uiso calc R 1 . . 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
  S  .0222(4)  .0185(4)  .0202(3)  -.0019(3)  .0072(3)  -.0044(3)
  P  .0254(4)  .0153(3)  .0144(3)  -.0009(3)  .0092(3)  .0010(3)
  O1  .0262(11)  .0238(11)  .0147(9)  .0020(9)  .0087(8)  .0036(8)
  O2  .0454(14)  .0147(10)  .0268(11)  .0005(10)  .0235(11)  -.0002(9)
  O3  .0325(13)  .0332(14)  .0466(14)  -.0091(11)  .0260(11)  -.0167(11)
  O4  .0320(12)  .0162(10)  .0205(10)  .0034(9)  .0149(9)  -.0004(8)
  O5  .0410(13)  .0226(11)  .0156(10)  -.0041(10)  .0110(9)  .0019(9)
  O6  .0260(11)  .0223(11)  .0216(10)  .0001(9)  .0143(9)  -.0028(8)
  O7  .0307(12)  .0128(10)  .0251(11)  .0002(9)  .0151(10)  .0009(8)
  N1  .0239(13)  .0178(12)  .0147(11)  .0026(10)  .0086(10)  -.0031(9)
  N2  .0230(12)  .0135(11)  .0145(11)  .0015(10)  .0093(10)  .0004(9)
  C1  .0231(15)  .0141(13)  .0163(13)  .0006(12)  .0080(12)  -.0006(11)
  C2  .0228(14)  .0144(13)  .0163(13)  .0000(11)  .0094(11)  -.0015(11)
  C3  .0232(14)  .0141(13)  .0155(12)  .0021(11)  .0097(11)  .0018(10)
  C4  .0242(15)  .0209(15)  .0176(13)  .0034(12)  .0097(12)  -.0007(11)
  C5  .0194(14)  .0202(15)  .0111(12)  -.0020(11)  .0043(11)  -.0022(11)
  C6  .0203(13)  .0138(12)  .0202(13)  .0026(12)  .0078(11)  -.0009(12)
  C7  .0240(15)  .0151(14)  .0182(14)  .0031(12)  .0097(12)  .0010(11)
  C8  .0238(15)  .0140(13)  .0215(14)  .0033(11)  .0112(13)  .0035(11)
  C9  .0185(14)  .0173(14)  .0168(13)  -.0001(11)  .0061(11)  .0011(11)
  C10  .0217(14)  .0213(15)  .0171(13)  .0013(13)  .0067(11)  -.0008(12)
  C11  .045(2)  .0191(15)  .0251(16)  .0125(15)  .0200(15)  .0003(13)
  C12  .0279(16)  .0163(14)  .0257(15)  .0041(12)  .0173(13)  .0002(12)
  C13  .0286(16)  .0189(15)  .0260(15)  -.0007(13)  .0115(13)  -.0002(13)
  C14  .0309(16)  .0228(16)  .0276(15)  -.0012(14)  .0136(13)  .0047(13)
  C15  .0265(17)  .0264(17)  .0221(15)  .0028(13)  .0105(13)  .0015(13)
  C16  .0252(16)  .0274(17)  .0301(17)  .0004(13)  .0063(14)  -.0061(13)
  C17  .0324(17)  .0154(15)  .0349(17)  -.0002(13)  .0188(14)  -.0006(13)
  C18  .0191(14)  .0142(13)  .0188(13)  -.0011(11)  .0098(12)  .0006(11)
  C19  .0203(15)  .0191(15)  .0210(14)  -.0008(12)  .0097(12)  .0027(11)
  C20  .038(2)  .0321(19)  .052(2)  -.0130(16)  .0354(19)  -.0178(17)
  C21  .044(2)  .034(2)  .076(3)  .0155(18)  .044(2)  .025(2)
  C22  .0318(17)  .0149(15)  .0305(16)  -.0031(12)  .0149(14)  -.0028(12)
  C23  .0355(18)  .0186(16)  .0382(19)  .0010(14)  .0190(16)  .0056(14)
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
  S C4 . 1.799(3) ?
  S C1 . 1.822(3) ?
  P O5 . 1.472(2) ?
  P O6 . 1.572(2) ?
  P O7 . 1.582(2) ?
  P C19 . 1.811(3) ?
  O1 C5 . 1.221(3) ?
  O2 C10 . 1.349(4) ?
  O2 C11 . 1.456(4) ?
  O3 C10 . 1.205(4) ?
  O4 C18 . 1.220(3) ?
  O6 C20 . 1.464(4) ?
  O7 C22 . 1.459(4) ?
  N1 C5 . 1.339(4) ?
  N1 C2 . 1.454(4) ?
  N1 H1N .  .8800 ?
  N2 C18 . 1.377(4) ?
  N2 C5 . 1.413(3) ?
  N2 C3 . 1.474(4) ?
  C1 C6 . 1.515(4) ?
  C1 C2 . 1.538(4) ?
  C1 H1 . 1.0000 ?
  C2 C3 . 1.562(4) ?
  C2 H2 . 1.0000 ?
  C3 C4 . 1.531(4) ?
  C3 H3 . 1.0000 ?
  C4 H4A .  .9900 ?
  C4 H4B .  .9900 ?
  C6 C7 . 1.520(4) ?
  C6 H6A .  .9900 ?
  C6 H6B .  .9900 ?
  C7 C8 . 1.521(4) ?
  C7 H7A .  .9900 ?
  C7 H7B .  .9900 ?
  C8 C9 . 1.518(4) ?
  C8 H8A .  .9900 ?
  C8 H8B .  .9900 ?
  C9 C10 . 1.492(4) ?
  C9 H9A .  .9900 ?
  C9 H9B .  .9900 ?
  C11 C12 . 1.509(4) ?
  C11 H11A .  .9900 ?
  C11 H11B .  .9900 ?
  C12 C17 . 1.382(4) ?
  C12 C13 . 1.398(4) ?
  C13 C14 . 1.384(4) ?
  C13 H13 .  .9500 ?
  C14 C15 . 1.379(4) ?
  C14 H14 .  .9500 ?
  C15 C16 . 1.376(5) ?
  C15 H15 .  .9500 ?
  C16 C17 . 1.391(4) ?
  C16 H16 .  .9500 ?
  C17 H17 .  .9500 ?
  C18 C19 . 1.517(4) ?
  C19 H19A .  .9900 ?
  C19 H19B .  .9900 ?
  C20 C21 . 1.488(5) ?
  C20 H20A .  .9900 ?
  C20 H20B .  .9900 ?
  C21 H21A .  .9800 ?
  C21 H21B .  .9800 ?
  C21 H21C .  .9800 ?
  C22 C23 . 1.489(4) ?
  C22 H22A .  .9900 ?
  C22 H22B .  .9900 ?
  C23 H23A .  .9800 ?
  C23 H23B .  .9800 ?
  C23 H23C .  .9800 ?