#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013282.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_2013282
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o231
_journal_page_last  o233
_publ_section_title
;
(+-)-5-(4-Methoxyphenylaminocarbonyl)-1-azabicyclo[3.3.0]octan-2-one
benzene solvate
;
loop_
_publ_author_name
  'Wheeler, Kraig A.'
_chemical_name_common  'N-(4-methoxyphenyl)proline peptidomimetic'
_chemical_formula_moiety  'C15 H18 N2 O3, C6 H6'
_chemical_formula_sum  'C21 H24 N2 O3'
_chemical_formula_iupac  'C15 H18 N2 O3, C6 H6'
_chemical_formula_weight  352.42
_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  9.7611(14)
_cell_length_b  10.1229(15)
_cell_length_c  10.7545(13)
_cell_angle_alpha  88.349(9)
_cell_angle_beta  87.715(9)
_cell_angle_gamma  62.925(9)
_cell_volume  945.4(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.238
_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_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
  O1 1.0387(4) 0.6505(4) 0.5250(3) 0.0442(8) Uani d P 0.50 A 1 O
  O2 0.68175(19) 0.6614(2) 0.10604(14) 0.0631(5) Uani d . 1 . . O
  O3 0.42561(17) 0.18987(17) 0.27697(13) 0.0479(4) Uani d . 1 . . O
  N1 0.9619(6) 0.6232(8) 0.3350(7) 0.0307(13) Uani d P 0.50 A 1 N
  N2 0.75634(19) 0.51634(18) 0.27993(15) 0.0366(4) Uani d . 1 . . N
  C1 0.8457(2) 0.7047(2) 0.24025(17) 0.0381(5) Uani d . 1 . . C
  C2 0.9390(8) 0.7214(8) 0.1341(7) 0.0515(19) Uani d P 0.50 A 1 C
  H2A 0.9659 0.8030 0.1477 0.062 Uiso calc PR 0.50 A 1 H
  H2B 0.8849 0.7391 0.0547 0.062 Uiso calc PR 0.50 A 1 H
  C3 1.0826(8) 0.5683(8) 0.1365(6) 0.0576(16) Uani d P 0.50 A 1 C
  H3A 1.0645 0.4942 0.0912 0.069 Uiso calc PR 0.50 A 1 H
  H3B 1.1732 0.5747 0.0979 0.069 Uiso calc PR 0.50 A 1 H
  C4 1.108(2) 0.526(2) 0.2746(13) 0.047(3) Uani d P 0.50 A 1 C
  H4A 1.1325 0.4205 0.2886 0.056 Uiso calc PR 0.50 A 1 H
  H4B 1.1924 0.5430 0.3059 0.056 Uiso calc PR 0.50 A 1 H
  C5 0.9436(5) 0.6885(5) 0.4438(4) 0.0303(8) Uani d P 0.50 A 1 C
  C6 0.7845(16) 0.8201(17) 0.4491(15) 0.054(3) Uani d P 0.50 A 1 C
  H6A 0.7878 0.9068 0.4865 0.065 Uiso calc PR 0.50 A 1 H
  H6B 0.7116 0.7953 0.4988 0.065 Uiso calc PR 0.50 A 1 H
  C7 0.7365(7) 0.8527(7) 0.3126(6) 0.0472(14) Uani d P 0.50 A 1 C
  H7A 0.7514 0.9376 0.2792 0.057 Uiso calc PR 0.50 A 1 H
  H7B 0.6270 0.8760 0.3051 0.057 Uiso calc PR 0.50 A 1 H
  O1A 1.1298(5) 0.5638(5) 0.4652(4) 0.0744(12) Uani d P 0.50 A 2 O
  N1A 0.9047(7) 0.6646(8) 0.3599(8) 0.0424(17) Uani d P 0.50 A 2 N
  C2A 0.7422(8) 0.8651(7) 0.2427(7) 0.0675(18) Uani d P 0.50 A 2 C
  H2BA 0.6619 0.8948 0.1796 0.081 Uiso calc PR 0.50 A 2 H
  H2BB 0.7994 0.9241 0.2302 0.081 Uiso calc PR 0.50 A 2 H
  C3A 0.6750(11) 0.8791(8) 0.3733(8) 0.090(3) Uani d P 0.50 A 2 C
  H3BA 0.5896 0.8517 0.3762 0.108 Uiso calc PR 0.50 A 2 H
  H3BB 0.6350 0.9822 0.4025 0.108 Uiso calc PR 0.50 A 2 H
  C4A 0.8061(19) 0.7728(16) 0.4546(15) 0.068(5) Uani d P 0.50 A 2 C
  H4BA 0.8600 0.8233 0.4927 0.081 Uiso calc PR 0.50 A 2 H
  H4BB 0.7691 0.7256 0.5207 0.081 Uiso calc PR 0.50 A 2 H
  C5A 1.0552(8) 0.5875(6) 0.3675(5) 0.0525(13) Uani d P 0.50 A 2 C
  C6A 1.120(2) 0.535(2) 0.2369(13) 0.062(4) Uani d P 0.50 A 2 C
  H6BA 1.1301 0.4351 0.2216 0.074 Uiso calc PR 0.50 A 2 H
  H6BB 1.2216 0.5337 0.2227 0.074 Uiso calc PR 0.50 A 2 H
  C7A 0.9959(9) 0.6547(9) 0.1544(8) 0.057(2) Uani d P 0.50 A 2 C
  H7BA 0.9859 0.6122 0.0755 0.069 Uiso calc PR 0.50 A 2 H
  H7BB 1.0196 0.7385 0.1355 0.069 Uiso calc PR 0.50 A 2 H
  C8 0.7535(2) 0.6241(2) 0.20196(18) 0.0391(5) Uani d . 1 . . C
  C9 0.6704(2) 0.4356(2) 0.27087(16) 0.0323(4) Uani d . 1 . . C
  C10 0.6211(2) 0.4088(2) 0.15977(17) 0.0398(5) Uani d . 1 . . C
  H10 0.6438 0.4464 0.0840 0.048 Uiso calc R 1 . . H
  C11 0.5383(2) 0.3270(2) 0.15840(17) 0.0391(5) Uani d . 1 . . C
  H11 0.5036 0.3103 0.0819 0.047 Uiso calc R 1 . . H
  C12 0.5070(2) 0.2706(2) 0.26785(18) 0.0369(4) Uani d . 1 . . C
  C13 0.5561(2) 0.2978(2) 0.37943(17) 0.0407(5) Uani d . 1 . . C
  H13 0.5339 0.2599 0.4552 0.049 Uiso calc R 1 . . H
  C14 0.6363(2) 0.3790(2) 0.38098(17) 0.0367(5) Uani d . 1 . . C
  H14 0.6691 0.3970 0.4579 0.044 Uiso calc R 1 . . H
  C15 0.3857(3) 0.1470(3) 0.1639(2) 0.0651(7) Uani d . 1 . . C
  H15A 0.3167 0.2359 0.1176 0.098 Uiso calc R 1 . . H
  H15B 0.3338 0.0854 0.1832 0.098 Uiso calc R 1 . . H
  H15C 0.4793 0.0903 0.1133 0.098 Uiso calc R 1 . . H
  C16 0.0365(3) 1.0360(3) 0.2883(2) 0.0625(7) Uani d . 1 . . C
  H16 -0.0479 1.1109 0.3328 0.075 Uiso calc R 1 . . H
  C17 0.0551(3) 1.0515(3) 0.1624(2) 0.0559(6) Uani d . 1 . . C
  H17 -0.0164 1.1369 0.1194 0.067 Uiso calc R 1 . . H
  C18 0.1777(3) 0.9428(3) 0.0988(2) 0.0536(6) Uani d . 1 . . C
  H18 0.1902 0.9528 0.0115 0.064 Uiso calc R 1 . . H
  C19 0.2825(3) 0.8194(3) 0.1611(2) 0.0503(6) Uani d . 1 . . C
  H19 0.3674 0.7447 0.1169 0.060 Uiso calc R 1 . . H
  C20 0.2641(3) 0.8046(3) 0.2871(2) 0.0542(6) Uani d . 1 . . C
  H20 0.3369 0.7203 0.3305 0.065 Uiso calc R 1 . . H
  C21 0.1406(3) 0.9115(3) 0.3498(2) 0.0645(7) Uani d . 1 . . C
  H21 0.1264 0.8999 0.4366 0.077 Uiso calc R 1 . . H
  HN2 0.802(2) 0.502(2) 0.3478(19) 0.047(6) Uiso d . 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
  O1 0.056(2) 0.0506(19) 0.0367(16) -0.0331(17) -0.0220(15) 0.0121(14)
  O2 0.0750(12) 0.0893(13) 0.0523(9) -0.0602(11) -0.0407(9) 0.0353(9)
  O3 0.0547(9) 0.0656(10) 0.0434(8) -0.0442(8) -0.0108(7) 0.0019(7)
  N1 0.020(3) 0.035(3) 0.040(3) -0.014(3) -0.017(3) 0.009(2)
  N2 0.0415(10) 0.0458(10) 0.0329(9) -0.0283(8) -0.0161(8) 0.0094(7)
  C1 0.0414(11) 0.0421(11) 0.0374(10) -0.0243(10) -0.0183(9) 0.0147(8)
  C2 0.064(5) 0.075(5) 0.039(3) -0.051(4) -0.021(3) 0.016(3)
  C3 0.057(4) 0.090(5) 0.040(3) -0.045(4) 0.002(3) -0.008(3)
  C4 0.032(5) 0.055(5) 0.050(6) -0.017(4) -0.004(4) -0.010(4)
  C5 0.032(2) 0.038(2) 0.030(2) -0.023(2) -0.0107(18) 0.0067(16)
  C6 0.035(3) 0.064(8) 0.055(4) -0.013(4) -0.010(3) -0.008(5)
  C7 0.050(4) 0.050(3) 0.042(4) -0.021(3) -0.015(3) -0.001(3)
  O1A 0.088(3) 0.100(3) 0.071(3) -0.072(3) -0.055(2) 0.049(2)
  N1A 0.042(4) 0.046(4) 0.049(4) -0.028(3) -0.021(3) 0.016(3)
  C2A 0.079(4) 0.055(3) 0.073(4) -0.034(3) -0.016(4) 0.015(4)
  C3A 0.126(8) 0.053(4) 0.084(5) -0.036(5) 0.008(5) 0.001(4)
  C4A 0.095(11) 0.076(10) 0.042(4) -0.047(9) 0.008(6) -0.012(5)
  C5A 0.061(4) 0.054(3) 0.062(4) -0.042(3) -0.023(3) 0.024(3)
  C6A 0.045(4) 0.059(5) 0.088(13) -0.030(4) 0.004(7) -0.009(8)
  C7A 0.056(6) 0.085(7) 0.049(4) -0.047(5) -0.012(4) 0.005(4)
  C8 0.0388(11) 0.0480(12) 0.0369(10) -0.0250(10) -0.0141(9) 0.0113(9)
  C9 0.0299(10) 0.0377(10) 0.0320(9) -0.0173(9) -0.0078(8) 0.0020(8)
  C10 0.0430(12) 0.0539(13) 0.0310(10) -0.0292(10) -0.0061(9) 0.0024(9)
  C11 0.0418(12) 0.0537(12) 0.0296(10) -0.0280(10) -0.0067(8) -0.0046(9)
  C12 0.0343(11) 0.0427(11) 0.0392(10) -0.0220(9) -0.0042(8) -0.0016(8)
  C13 0.0460(12) 0.0529(12) 0.0322(10) -0.0303(11) -0.0051(9) 0.0049(9)
  C14 0.0426(12) 0.0461(11) 0.0288(9) -0.0260(10) -0.0108(8) 0.0014(8)
  C15 0.0860(19) 0.0836(18) 0.0572(14) -0.0645(17) -0.0208(13) -0.0006(13)
  C16 0.0557(16) 0.0591(15) 0.0671(16) -0.0213(13) 0.0075(13) -0.0120(13)
  C17 0.0566(15) 0.0566(15) 0.0642(15) -0.0335(13) -0.0205(12) 0.0130(12)
  C18 0.0637(16) 0.0771(17) 0.0391(11) -0.0485(15) -0.0092(11) 0.0053(11)
  C19 0.0499(14) 0.0634(15) 0.0444(12) -0.0317(12) 0.0021(10) -0.0070(11)
  C20 0.0581(15) 0.0565(14) 0.0459(13) -0.0242(12) -0.0081(11) 0.0056(11)
  C21 0.0764(19) 0.0707(17) 0.0394(12) -0.0280(15) 0.0040(12) -0.0001(12)
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
  O2 C8 . 1.222(2) ?
  O3 C12 . 1.374(2) ?
  O3 C15 . 1.429(2) ?
  N2 C8 . 1.347(2) ?
  N2 C9 . 1.420(2) ?
  N2 HN2 . 0.84(2) ?
  C1 N1A . 1.403(9) ?
  C1 C2A . 1.472(7) ?
  C1 N1 . 1.482(7) ?
  C1 C2 . 1.486(8) ?
  C1 C8 . 1.537(3) ?
  C1 C7A . 1.582(9) ?
  C1 C7 . 1.592(7) ?
  C9 C10 . 1.384(2) ?
  C9 C14 . 1.394(3) ?
  C10 C11 . 1.397(3) ?
  C10 H10 . 0.9500 ?
  C11 C12 . 1.377(3) ?
  C11 H11 . 0.9500 ?
  C12 C13 . 1.390(3) ?
  C13 C14 . 1.370(3) ?
  C13 H13 . 0.9500 ?
  C14 H14 . 0.9500 ?
  C15 H15A . 0.9800 ?
  C15 H15B . 0.9800 ?
  C15 H15C . 0.9800 ?
  C16 C17 . 1.373(3) ?
  C16 C21 . 1.378(3) ?
  C16 H16 . 0.9500 ?
  C17 C18 . 1.375(3) ?
  C17 H17 . 0.9500 ?
  C18 C19 . 1.378(3) ?
  C18 H18 . 0.9500 ?
  C19 C20 . 1.372(3) ?
  C19 H19 . 0.9500 ?
  C20 C21 . 1.368(3) ?
  C20 H20 . 0.9500 ?
  C21 H21 . 0.9500 ?
  O1 C5 . 1.221(4) ?
  N1 C5 . 1.326(9) ?
  N1 C4 . 1.451(18) ?
  C2 C3 . 1.547(9) ?
  C2 H2A . 0.9900 ?
  C2 H2B . 0.9900 ?
  C3 C4 . 1.532(14) ?
  C3 H3A . 0.9900 ?
  C3 H3B . 0.9900 ?
  C4 H4A . 0.9900 ?
  C4 H4B . 0.9900 ?
  C5 C6 . 1.518(14) ?
  C6 C7 . 1.539(17) ?
  C6 H6A . 0.9900 ?
  C6 H6B . 0.9900 ?
  C7 H7A . 0.9900 ?
  C7 H7B . 0.9900 ?
  O1A C5A . 1.256(6) ?
  N1A C5A . 1.318(8) ?
  N1A C4A . 1.480(17) ?
  C2A C3A . 1.509(9) ?
  C2A H2BA . 0.9900 ?
  C2A H2BB . 0.9900 ?
  C3A C4A . 1.530(17) ?
  C3A H3BA . 0.9900 ?
  C3A H3BB . 0.9900 ?
  C4A H4BA . 0.9900 ?
  C4A H4BB . 0.9900 ?
  C5A C6A . 1.524(16) ?
  C6A C7A . 1.553(19) ?
  C6A H6BA . 0.9900 ?
  C6A H6BB . 0.9900 ?
  C7A H7BA . 0.9900 ?
  C7A H7BB . 0.9900 ?
_cod_database_code 2013282