#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2202945.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_2202945
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o952
_journal_page_last  o954
_publ_section_title
;
L-Phenylalanine fumaric acid
;
loop_
_publ_author_name
  'M.Alagar'
  'R.V. Krishnakumar'
  'K.Rajagopal'
  'M. Subha Nandhini'
  'S.Natarajan'
_chemical_formula_moiety  'C9 H11 N O2, C4 H4 O4'
_chemical_formula_sum            'C13 H15 N O6'
_[local]_cod_chemical_formula_sum_orig 'C13 H15 N1 O6'
_chemical_formula_weight  281.26
_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'
_cell_length_a  5.7016(10)
_cell_length_b  11.4864(15)
_cell_length_c  11.5542(17)
_cell_angle_alpha  67.953(11)
_cell_angle_beta  81.158(13)
_cell_angle_gamma  79.379(15)
_cell_volume  686.37(19)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.361
_exptl_crystal_density_meas  1.35(2)
_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
  O1 1.2177(3) 0.5907(2) 0.15771(18) 0.0444(6) Uani d . 1 . . O
  O2 1.0094(3) 0.64490(19) 0.31153(16) 0.0334(4) Uani d . 1 . . O
  O3 0.8382(4) 0.5849(2) 0.54851(19) 0.0491(6) Uani d . 1 . . O
  H3 0.8806 0.5960 0.4745 0.074 Uiso calc R 1 . . H
  O4 0.4730(4) 0.6316(2) 0.48204(18) 0.0435(5) Uani d . 1 . . O
  O5 0.3373(4) 0.5769(3) 0.9349(2) 0.0646(8) Uani d . 1 . . O
  H5 0.2763 0.5919 0.9978 0.097 Uiso calc R 1 . . H
  O6 -0.0355(4) 0.6312(3) 0.8789(2) 0.0744(9) Uani d . 1 . . O
  O1' -0.2517(3) -0.08448(19) 0.13858(17) 0.0387(5) Uani d . 1 . . O
  O2' -0.3549(3) -0.0946(2) 0.33444(18) 0.0435(5) Uani d . 1 . . O
  O3' -0.0096(4) 0.9407(3) 0.9166(2) 0.0583(7) Uani d . 1 . . O
  H3' -0.0619 0.9322 0.9891 0.087 Uiso calc R 1 . . H
  O4' 0.3397(4) 0.8650(2) 0.99990(19) 0.0576(7) Uani d . 1 . . O
  O5' 0.5047(4) 0.9449(3) 0.5405(2) 0.0668(8) Uani d . 1 . . O
  H5' 0.5739 0.9506 0.4713 0.100 Uiso calc R 1 . . H
  O6' 0.8757(4) 0.8889(3) 0.5960(2) 0.0570(7) Uani d . 1 . . O
  N1 0.5858(4) 0.6716(2) 0.21939(19) 0.0316(5) Uani d . 1 . . N
  H1A 0.4555 0.6652 0.1897 0.047 Uiso calc R 1 . . H
  H1B 0.6013 0.7531 0.1971 0.047 Uiso calc R 1 . . H
  H1C 0.5721 0.6360 0.3027 0.047 Uiso calc R 1 . . H
  N1' 0.1311(4) -0.1469(2) 0.3734(2) 0.0367(5) Uani d . 1 . . N
  H1'1 0.2788 -0.1348 0.3777 0.055 Uiso calc R 1 . . H
  H1'2 0.1312 -0.2274 0.3825 0.055 Uiso calc R 1 . . H
  H1'3 0.0328 -0.1291 0.4341 0.055 Uiso calc R 1 . . H
  C1 1.0254(5) 0.6161(3) 0.2165(2) 0.0297(6) Uani d . 1 . . C
  C2 0.8006(4) 0.6057(3) 0.1671(2) 0.0309(6) Uani d . 1 . . C
  H2 0.8155 0.6490 0.0758 0.037 Uiso calc R 1 . . H
  C3 0.7768(5) 0.4663(3) 0.1947(3) 0.0431(7) Uani d . 1 . . C
  H3A 0.6263 0.4634 0.1672 0.052 Uiso calc R 1 . . H
  H3B 0.9049 0.4327 0.1453 0.052 Uiso calc R 1 . . H
  C4 0.7852(6) 0.3813(3) 0.3305(3) 0.0469(8) Uani d . 1 . . C
  C5 0.9960(7) 0.3078(4) 0.3747(4) 0.0651(11) Uani d . 1 . . C
  H5A 1.1347 0.3112 0.3200 0.078 Uiso calc R 1 . . H
  C6 1.0033(10) 0.2292(4) 0.4992(5) 0.0872(16) Uani d . 1 . . C
  H6 1.1463 0.1793 0.5269 0.105 Uiso calc R 1 . . H
  C7 0.8036(12) 0.2240(5) 0.5817(5) 0.0909(16) Uani d . 1 . . C
  H7 0.8100 0.1718 0.6655 0.109 Uiso calc R 1 . . H
  C8 0.5908(10) 0.2975(5) 0.5391(4) 0.0829(13) Uani d . 1 . . C
  H8 0.4536 0.2950 0.5946 0.100 Uiso calc R 1 . . H
  C9 0.5819(7) 0.3741(4) 0.4150(4) 0.0622(10) Uani d . 1 . . C
  H9 0.4374 0.4219 0.3872 0.075 Uiso calc R 1 . . H
  C10 0.6026(5) 0.6082(3) 0.5643(3) 0.0359(7) Uani d . 1 . . C
  C11 0.5129(5) 0.6016(3) 0.6938(2) 0.0377(7) Uani d . 1 . . C
  H11 0.6204 0.5928 0.7504 0.045 Uiso calc R 1 . . H
  C12 0.2810(5) 0.6082(3) 0.7287(3) 0.0411(7) Uani d . 1 . . C
  H12 0.1775 0.6139 0.6713 0.049 Uiso calc R 1 . . H
  C13 0.1762(6) 0.6070(3) 0.8556(3) 0.0444(8) Uani d . 1 . . C
  C1' -0.2059(5) -0.0818(3) 0.2398(2) 0.0307(6) Uani d . 1 . . C
  C2' 0.0482(5) -0.0623(3) 0.2493(2) 0.0321(6) Uani d . 1 . . C
  H2' 0.1559 -0.0847 0.1838 0.039 Uiso calc R 1 . . H
  C3' 0.0625(6) 0.0752(3) 0.2302(3) 0.0455(8) Uani d . 1 . . C
  H3'1 -0.0641 0.1037 0.2839 0.055 Uiso calc R 1 . . H
  H3'2 0.2148 0.0802 0.2545 0.055 Uiso calc R 1 . . H
  C4' 0.0386(6) 0.1612(3) 0.0959(3) 0.0475(8) Uani d . 1 . . C
  C5' -0.1791(7) 0.2338(3) 0.0585(4) 0.0628(10) Uani d . 1 . . C
  H5'1 -0.3109 0.2318 0.1173 0.075 Uiso calc R 1 . . H
  C6' -0.1996(10) 0.3090(4) -0.0661(6) 0.0899(17) Uani d . 1 . . C
  H6' -0.3459 0.3567 -0.0908 0.108 Uiso calc R 1 . . H
  C7' -0.0076(12) 0.3139(4) -0.1529(5) 0.0903(17) Uani d . 1 . . C
  H7' -0.0228 0.3652 -0.2364 0.108 Uiso calc R 1 . . H
  C8' 0.2109(10) 0.2424(5) -0.1171(4) 0.0885(15) Uani d . 1 . . C
  H8' 0.3424 0.2455 -0.1763 0.106 Uiso calc R 1 . . H
  C9' 0.2316(8) 0.1668(4) 0.0068(4) 0.0662(10) Uani d . 1 . . C
  H9' 0.3780 0.1187 0.0308 0.079 Uiso calc R 1 . . H
  C10' 0.2233(6) 0.9046(3) 0.9116(3) 0.0411(7) Uani d . 1 . . C
  C11' 0.3249(6) 0.9177(3) 0.7809(3) 0.0432(7) Uani d . 1 . . C
  H11' 0.2207 0.9369 0.7198 0.052 Uiso calc R 1 . . H
  C12' 0.5558(6) 0.9031(3) 0.7497(3) 0.0461(8) Uani d . 1 . . C
  H12' 0.6583 0.8867 0.8110 0.055 Uiso calc R 1 . . H
  C13' 0.6629(6) 0.9112(3) 0.6226(3) 0.0415(7) 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
  O1 0.0214(10) 0.0850(16) 0.0390(11) -0.0062(10) 0.0017(8) -0.0384(11)
  O2 0.0288(10) 0.0518(12) 0.0259(9) -0.0084(8) -0.0007(7) -0.0203(9)
  O3 0.0349(12) 0.0846(17) 0.0295(10) -0.0066(11) 0.0023(9) -0.0248(12)
  O4 0.0383(11) 0.0658(14) 0.0257(10) 0.0002(10) -0.0044(9) -0.0185(9)
  O5 0.0410(13) 0.125(2) 0.0379(13) -0.0009(14) -0.0006(10) -0.0463(15)
  O6 0.0396(15) 0.136(3) 0.0395(13) 0.0061(15) 0.0027(10) -0.0331(15)
  O1' 0.0364(11) 0.0551(12) 0.0281(10) -0.0076(9) -0.0051(8) -0.0174(9)
  O2' 0.0308(11) 0.0737(14) 0.0320(11) -0.0111(10) 0.0006(8) -0.0252(10)
  O3' 0.0423(13) 0.107(2) 0.0307(11) -0.0080(13) 0.0003(9) -0.0326(13)
  O4' 0.0548(15) 0.0835(18) 0.0320(12) 0.0068(13) -0.0071(10) -0.0243(12)
  O5' 0.0401(13) 0.128(2) 0.0357(12) -0.0035(14) -0.0003(10) -0.0382(15)
  O6' 0.0384(14) 0.0931(19) 0.0406(13) 0.0020(12) -0.0008(10) -0.0315(13)
  N1 0.0207(10) 0.0502(13) 0.0267(11) -0.0040(9) -0.0010(8) -0.0180(10)
  N1' 0.0291(12) 0.0482(14) 0.0327(12) -0.0009(10) -0.0048(10) -0.0155(11)
  C1 0.0270(14) 0.0392(15) 0.0239(12) -0.0039(11) -0.0022(10) -0.0128(11)
  C2 0.0224(12) 0.0495(16) 0.0241(12) -0.0054(11) -0.0004(10) -0.0173(12)
  C3 0.0304(15) 0.059(2) 0.0532(18) -0.0069(14) -0.0043(13) -0.0345(16)
  C4 0.0449(18) 0.0426(18) 0.063(2) -0.0090(14) -0.0119(15) -0.0262(16)
  C5 0.058(2) 0.049(2) 0.091(3) -0.0016(18) -0.023(2) -0.024(2)
  C6 0.094(4) 0.050(3) 0.110(4) -0.002(2) -0.049(3) -0.008(3)
  C7 0.126(5) 0.068(3) 0.074(3) -0.035(3) -0.035(3) 0.001(2)
  C8 0.092(3) 0.083(3) 0.065(3) -0.029(3) -0.002(2) -0.010(2)
  C9 0.054(2) 0.065(2) 0.061(2) -0.0142(18) -0.0051(18) -0.0135(19)
  C10 0.0363(16) 0.0427(17) 0.0263(14) -0.0044(13) -0.0005(12) -0.0112(12)
  C11 0.0416(17) 0.0505(18) 0.0211(13) -0.0048(14) -0.0025(12) -0.0138(13)
  C12 0.0396(18) 0.0572(19) 0.0276(14) -0.0042(14) -0.0020(12) -0.0181(14)
  C13 0.0399(18) 0.063(2) 0.0295(15) -0.0041(14) 0.0005(13) -0.0186(14)
  C1' 0.0300(14) 0.0339(15) 0.0294(14) -0.0032(12) -0.0043(11) -0.0126(11)
  C2' 0.0314(14) 0.0401(15) 0.0264(13) -0.0050(11) -0.0011(10) -0.0143(11)
  C3' 0.0489(18) 0.0450(18) 0.0489(18) -0.0091(14) -0.0125(14) -0.0195(15)
  C4' 0.0521(19) 0.0384(17) 0.055(2) -0.0104(14) -0.0132(15) -0.0148(15)
  C5' 0.061(2) 0.042(2) 0.081(3) -0.0008(17) -0.017(2) -0.0161(19)
  C6' 0.093(4) 0.053(3) 0.108(4) -0.005(2) -0.054(3) 0.003(3)
  C7' 0.128(5) 0.066(3) 0.062(3) -0.027(3) -0.038(3) 0.011(2)
  C8' 0.111(4) 0.083(3) 0.057(3) -0.035(3) -0.002(3) -0.001(2)
  C9' 0.059(2) 0.071(3) 0.058(2) -0.0121(19) -0.0060(18) -0.0087(19)
  C10' 0.0461(18) 0.0507(19) 0.0316(16) -0.0065(14) -0.0020(14) -0.0210(14)
  C11' 0.0444(19) 0.057(2) 0.0303(15) -0.0056(14) -0.0051(13) -0.0183(14)
  C12' 0.046(2) 0.067(2) 0.0307(15) -0.0052(16) -0.0036(13) -0.0243(15)
  C13' 0.0410(18) 0.0550(19) 0.0321(15) -0.0051(14) -0.0044(12) -0.0198(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
  O1 C1 . 1.245(3) y
  O2 C1 . 1.247(3) y
  N1 C2 . 1.488(3) y
  C1 C2 . 1.521(3) y
  C2 C3 . 1.539(4) y
  C3 C4 . 1.508(5) y
  O3 C10 . 1.318(4) y
  O3 H3 . 0.8200 ?
  O4 C10 . 1.214(4) y
  O5 C13 . 1.307(4) y
  O5 H5 . 0.8200 ?
  O6 C13 . 1.200(4) y
  O1' C1' . 1.249(3) y
  O2' C1' . 1.257(3) y
  N1' C2' . 1.488(3) y
  C1' C2' . 1.533(4) y
  C2' C3' . 1.526(4) y
  C3' C4' . 1.506(4) y
  O3' C10' . 1.315(4) y
  O3' H3' . 0.8200 ?
  O4' C10' . 1.199(4) y
  O5' C13' . 1.313(4) y
  O5' H5' . 0.8200 ?
  O6' C13' . 1.209(4) y
  N1 H1A . 0.8900 ?
  N1 H1B . 0.8900 ?
  N1 H1C . 0.8900 ?
  N1' H1'1 . 0.8900 ?
  N1' H1'2 . 0.8900 ?
  N1' H1'3 . 0.8900 ?
  C2 H2 . 0.9800 ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 C5 . 1.381(5) ?
  C4 C9 . 1.390(5) ?
  C5 C6 . 1.384(7) ?
  C5 H5A . 0.9300 ?
  C6 C7 . 1.363(8) ?
  C6 H6 . 0.9300 ?
  C7 C8 . 1.386(8) ?
  C7 H7 . 0.9300 ?
  C8 C9 . 1.375(6) ?
  C8 H8 . 0.9300 ?
  C9 H9 . 0.9300 ?
  C10 C11 . 1.483(4) .
  C11 C12 . 1.319(4) .
  C11 H11 . 0.9300 ?
  C12 C13 . 1.491(4) .
  C12 H12 . 0.9300 ?
  C2' H2' . 0.9800 ?
  C3' H3'1 . 0.9700 ?
  C3' H3'2 . 0.9700 ?
  C4' C9' . 1.379(5) ?
  C4' C5' . 1.391(5) ?
  C5' C6' . 1.384(7) ?
  C5' H5'1 . 0.9300 ?
  C6' C7' . 1.360(8) ?
  C6' H6' . 0.9300 ?
  C7' C8' . 1.387(8) ?
  C7' H7' . 0.9300 ?
  C8' C9' . 1.379(6) ?
  C8' H8' . 0.9300 ?
  C9' H9' . 0.9300 ?
  C10' C11' . 1.493(4) .
  C11' C12' . 1.307(5) .
  C11' H11' . 0.9300 ?
  C12' C13' . 1.477(4) .
  C12' H12' . 0.9300 ?
_cod_database_code 2202945