#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200170.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_2200170
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o192
_journal_page_last  o194
_publ_section_title
;
L-Phenylalanine nitrate (4/1)
;
loop_
_publ_author_name
  'G\"orbitz, Carl Henrik'
_chemical_formula_moiety  'C9 H12 N1 O2 1+, N1 O3 1-, 3C9 H11 N1 O2'
_chemical_formula_sum  'C9 H11.25 N1.25 O2.75'
_chemical_formula_iupac  'C9 H12 N1 O2 1+, N1 O3 1-, 3C9 H11 N1 O2'
_chemical_formula_weight  180.95
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z'
_cell_length_a  30.285(8)
_cell_length_b  5.3022(13)
_cell_length_c  22.317(6)
_cell_angle_alpha  90.00
_cell_angle_beta  102.263(4)
_cell_angle_gamma  90.00
_cell_volume  3501.9(15)
_cell_formula_units_Z  16
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.373
_diffrn_ambient_temperature  150(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
  O1A  .3062(2)  .3387(13)  .0591(3)  .0298(15) Uani d U 1 . . O
  O2A  .3194(2)  .1777(13)  .1536(3)  .0335(16) Uani d U 1 . . O
  HO2A  .3151  .3546  .1674  .050 Uiso d R 1 . . H
  N1A  .29139(18)  -.1575(13)  .0158(3)  .0210(16) Uani d DU 1 . . N
  H1A  .2961  -.3174  .0037  .032 Uiso calc R 1 . . H
  H2A  .2935  -.0477  -.0149  .032 Uiso calc R 1 . . H
  H3A  .2634  -.1465  .0243  .032 Uiso calc R 1 . . H
  C1A  .3157(2)  .1668(13)  .0959(3)  .0178(17) Uani d DU 1 . . C
  C2A  .32619(19)  -.0934(13)  .0718(3)  .0236(19) Uani d DU 1 . . C
  H21A  .3246  -.2220  .1040  .028 Uiso calc R 1 . . H
  C3A  .37314(18)  -.1053(15)  .0571(3)  .033(2) Uani d DU 1 . . C
  H31A  .3806  -.2843  .0514  .039 Uiso calc R 1 . . H
  H32A  .3721  -.0177  .0176  .039 Uiso calc R 1 . . H
  C4A  .4108(2)  .0093(14)  .1049(3)  .029(2) Uani d DU 1 . . C
  C5A  .4215(3)  -.0852(15)  .1646(3)  .032(2) Uani d DU 1 . . C
  H51A  .4056  -.2277  .1751  .038 Uiso calc R 1 . . H
  C6A  .4549(3)  .0266(18)  .2088(3)  .042(3) Uani d DU 1 . . C
  H61A  .4621  -.0404  .2492  .050 Uiso calc R 1 . . H
  C7A  .4775(3)  .2355(16)  .1940(3)  .040(3) Uani d DU 1 . . C
  H71A  .5001  .3141  .2243  .048 Uiso calc R 1 . . H
  C8A  .4673(3)  .3305(16)  .1347(3)  .043(3) Uani d DU 1 . . C
  H81A  .4830  .4739  .1246  .051 Uiso calc R 1 . . H
  C9A  .4340(3)  .2178(15)  .0898(3)  .040(3) Uani d DU 1 . . C
  H91A  .4273  .2830  .0492  .048 Uiso calc R 1 . . H
  O1B  .2901(2)  .3968(13)  .2706(3)  .0302(15) Uani d U 1 . . O
  O2B  .3250(2)  .5881(14)  .2045(3)  .0359(17) Uani d U 1 . . O
  N1B  .3060(2)  .7650(15)  .3540(3)  .0309(19) Uani d DU 1 . . N
  H1B  .3121  .9037  .3784  .046 Uiso calc R 1 . . H
  H2B  .3223  .6318  .3726  .046 Uiso calc R 1 . . H
  H3B  .2760  .7286  .3477  .046 Uiso calc R 1 . . H
  C1B  .3115(3)  .5761(14)  .2543(3)  .023(2) Uani d DU 1 . . C
  C2B  .3184(2)  .8158(13)  .2940(3)  .025(2) Uani d DU 1 . . C
  H21B  .2974  .9478  .2724  .030 Uiso calc R 1 . . H
  C3B  .36626(19)  .9197(12)  .3036(3)  .028(2) Uani d DU 1 . . C
  H31B  .3737  .9430  .2628  .033 Uiso calc R 1 . . H
  H32B  .3668 1.0883  .3227  .033 Uiso calc R 1 . . H
  C4B  .4029(2)  .7602(12)  .3425(2)  .0198(18) Uani d DU 1 . . C
  C5B  .4225(3)  .5587(14)  .3174(3)  .029(2) Uani d DU 1 . . C
  H51B  .4136  .5237  .2748  .035 Uiso calc R 1 . . H
  C6B  .4551(3)  .4090(14)  .3541(3)  .033(2) Uani d DU 1 . . C
  H61B  .4685  .2735  .3366  .040 Uiso calc R 1 . . H
  C7B  .4678(3)  .4571(15)  .4161(3)  .031(2) Uani d DU 1 . . C
  H71B  .4898  .3536  .4414  .037 Uiso calc R 1 . . H
  C8B  .4485(3)  .6574(15)  .4415(3)  .033(2) Uani d DU 1 . . C
  H81B  .4576  .6913  .4841  .039 Uiso calc R 1 . . H
  C9B  .4159(3)  .8092(14)  .4049(3)  .030(2) Uani d DU 1 . . C
  H91B  .4027  .9452  .4226  .036 Uiso calc R 1 . . H
  O1C  .2980(2)  .0210(13)  .4784(3)  .0292(15) Uani d U 1 . . O
  O2C  .3302(2)  .2695(14)  .4186(3)  .0348(17) Uani d U 1 . . O
  N1C  .2911(2)  .3854(14)  .5580(3)  .0249(17) Uani d DU 1 . . N
  H1C  .2992  .4900  .5908  .037 Uiso calc R 1 . . H
  H2C  .2966  .2228  .5703  .037 Uiso calc R 1 . . H
  H3C  .2612  .4050  .5414  .037 Uiso calc R 1 . . H
  C1C  .3156(3)  .2316(14)  .4652(3)  .0215(19) Uani d DU 1 . . C
  C2C  .3179(2)  .4485(13)  .5112(3)  .0220(19) Uani d DU 1 . . C
  H21C  .3036  .5995  .4881  .026 Uiso calc R 1 . . H
  C3C  .3661(2)  .5201(12)  .5420(3)  .026(2) Uani d DU 1 . . C
  H31C  .3831  .5539  .5097  .031 Uiso calc R 1 . . H
  H32C  .3651  .6793  .5649  .031 Uiso calc R 1 . . H
  C4C  .3918(2)  .3257(13)  .5857(2)  .027(2) Uani d DU 1 . . C
  C5C  .4210(3)  .1543(14)  .5665(3)  .028(2) Uani d DU 1 . . C
  H51C  .4253  .1609  .5256  .033 Uiso calc R 1 . . H
  C6C  .4437(3)  -.0257(15)  .6068(3)  .039(3) Uani d DU 1 . . C
  H61C  .4622  -.1473  .5928  .047 Uiso calc R 1 . . H
  C7C  .4395(3)  -.0277(17)  .6671(3)  .043(3) Uani d DU 1 . . C
  H71C  .4558  -.1470  .6950  .052 Uiso calc R 1 . . H
  C8C  .4112(3)  .1455(18)  .6869(3)  .047(3) Uani d DU 1 . . C
  H81C  .4080  .1423  .7283  .056 Uiso calc R 1 . . H
  C9C  .3876(3)  .3240(15)  .6465(3)  .037(2) Uani d DU 1 . . C
  H91C  .3687  .4437  .6604  .044 Uiso calc R 1 . . H
  O1D  .2777(2)  .4577(13)  .9240(3)  .0289(15) Uani d U 1 . . O
  O2D  .3019(3)  .0734(13)  .9050(3)  .0343(17) Uani d U 1 . . O
  N1D  .2841(2)  .6584(11)  .8188(3)  .0273(17) Uani d DU 1 . . N
  H1D  .2920  .7192  .7845  .041 Uiso calc R 1 . . H
  H2D  .2977  .7516  .8518  .041 Uiso calc R 1 . . H
  H3D  .2536  .6680  .8144  .041 Uiso calc R 1 . . H
  C1D  .2928(3)  .2989(15)  .8913(3)  .0235(19) Uani d DU 1 . . C
  C2D  .29870(19)  .3903(12)  .8283(3)  .0209(18) Uani d DU 1 . . C
  H21D  .2779  .2876  .7967  .025 Uiso calc R 1 . . H
  C3D  .34613(19)  .3540(12)  .8177(3)  .027(2) Uani d DU 1 . . C
  H31D  .3452  .3784  .7735  .033 Uiso calc R 1 . . H
  H32D  .3551  .1769  .8277  .033 Uiso calc R 1 . . H
  C4D  .3827(2)  .5236(14)  .8534(2)  .025(2) Uani d DU 1 . . C
  C5D  .3988(3)  .4946(18)  .9164(3)  .043(3) Uani d DU 1 . . C
  H51D  .3859  .3695  .9379  .052 Uiso calc R 1 . . H
  C6D  .4334(3)  .6461(19)  .9480(3)  .046(3) Uani d DU 1 . . C
  H61D  .4443  .6228  .9908  .055 Uiso calc R 1 . . H
  C7D  .4519(3)  .8308(17)  .9173(3)  .039(2) Uani d DU 1 . . C
  H71D  .4753  .9363  .9388  .047 Uiso calc R 1 . . H
  C8D  .4361(3)  .8612(17)  .8546(3)  .044(3) Uani d DU 1 . . C
  H81D  .4484  .9906  .8335  .053 Uiso calc R 1 . . H
  C9D  .4025(3)  .7039(15)  .8222(2)  .033(2) Uani d DU 1 . . C
  H91D  .3931  .7198  .7789  .040 Uiso calc R 1 . . H
  O1E  .2868(2)  -.1140(14)  .6098(3)  .0385(17) Uani d U 1 . . O
  O2E  .2882(3)  .1299(15)  .6877(3)  .0401(19) Uani d U 1 . . O
  O3E  .3071(3)  -.2648(19)  .7011(4)  .060(2) Uani d U 1 . . O
  N1E  .2944(3)  -.0867(17)  .6663(3)  .0314(19) Uani d U 1 . . N
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
  O1A  .048(3)  .008(3)  .030(3)  -.001(3)  .000(2)  .000(2)
  O2A  .057(4)  .008(3)  .033(3)  -.002(3)  .004(3)  -.003(3)
  N1A  .030(3)  .008(3)  .023(3)  .000(3)  .001(2)  -.001(2)
  C1A  .022(4)  .007(4)  .021(3)  -.001(3)  -.001(3)  .001(3)
  C2A  .038(4)  .006(4)  .024(3)  -.002(3)  .001(3)  .001(3)
  C3A  .040(4)  .023(4)  .034(4)  .003(4)  .005(3)  -.001(4)
  C4A  .036(4)  .014(4)  .034(4)  -.001(4)  .005(3)  .000(3)
  C5A  .041(4)  .024(4)  .032(4)  -.001(4)  .008(3)  .001(4)
  C6A  .043(5)  .039(5)  .039(4)  -.002(4)  .002(4)  -.005(4)
  C7A  .037(4)  .033(5)  .048(4)  -.001(4)  .006(4)  -.009(4)
  C8A  .043(5)  .030(5)  .053(5)  -.005(4)  .006(4)  -.002(4)
  C9A  .045(5)  .027(5)  .046(4)  .002(4)  .003(4)  .005(4)
  O1B  .044(3)  .010(3)  .037(3)  -.007(3)  .009(2)  -.009(3)
  O2B  .054(3)  .018(3)  .035(3)  -.006(3)  .007(2)  -.006(2)
  N1B  .033(4)  .022(4)  .037(4)  .006(3)  .006(3)  -.008(3)
  C1B  .029(4)  .009(4)  .029(4)  .002(3)  -.001(3)  .001(3)
  C2B  .037(4)  .013(4)  .024(4)  .003(4)  .002(3)  -.002(3)
  C3B  .038(4)  .012(4)  .032(4)  .004(4)  .004(3)  -.002(3)
  C4B  .024(4)  .009(4)  .027(4)  -.005(3)  .006(3)  -.005(3)
  C5B  .037(4)  .020(4)  .028(4)  .002(4)  .002(3)  .001(3)
  C6B  .038(4)  .018(4)  .043(4)  .001(4)  .006(3)  -.006(4)
  C7B  .029(4)  .026(4)  .036(4)  .005(4)  .003(3)  .001(4)
  C8B  .034(4)  .027(4)  .035(4)  -.004(4)  .003(3)  -.002(4)
  C9B  .029(4)  .025(4)  .035(4)  .000(4)  .007(3)  -.005(4)
  O1C  .041(3)  .007(3)  .037(3)  -.004(3)  .001(3)  -.003(3)
  O2C  .048(4)  .020(3)  .036(3)  .005(3)  .009(3)  -.005(3)
  N1C  .033(3)  .009(3)  .031(3)  -.001(3)  .003(3)  -.002(3)
  C1C  .029(4)  .008(4)  .024(4)  -.003(3)  -.001(3)  -.002(3)
  C2C  .024(4)  .010(4)  .031(4)  .004(3)  .003(3)  .000(3)
  C3C  .034(4)  .011(4)  .033(4)  .000(4)  .007(3)  .001(3)
  C4C  .028(4)  .023(4)  .028(4)  -.008(4)  .002(3)  -.004(3)
  C5C  .025(4)  .021(4)  .035(4)  -.001(4)  .001(3)  .000(4)
  C6C  .044(5)  .023(4)  .047(4)  -.001(4)  .003(4)  -.007(4)
  C7C  .047(5)  .032(5)  .048(4)  .004(4)  .005(4)  .006(4)
  C8C  .049(5)  .049(5)  .041(4)  .004(5)  .007(4)  .006(4)
  C9C  .044(5)  .027(5)  .038(4)  .004(4)  .008(3)  .003(4)
  O1D  .042(3)  .017(3)  .030(3)  -.002(3)  .013(2)  -.003(3)
  O2D  .058(4)  .008(3)  .036(3)  -.006(3)  .008(3)  .001(3)
  N1D  .039(4)  .009(3)  .031(3)  .001(3)  .001(3)  .000(3)
  C1D  .031(4)  .013(4)  .026(4)  -.005(4)  .004(3)  -.003(3)
  C2D  .026(3)  .008(3)  .025(3)  .000(3)  -.001(3)  -.001(3)
  C3D  .038(4)  .012(4)  .031(4)  .002(4)  .006(3)  .005(3)
  C4D  .031(4)  .020(4)  .028(4)  -.002(4)  .009(3)  .000(3)
  C5D  .050(5)  .038(5)  .041(4)  -.011(4)  .009(4)  .007(4)
  C6D  .047(5)  .048(5)  .043(4)  -.005(4)  .011(4)  .002(4)
  C7D  .037(4)  .027(5)  .049(4)  -.001(4)  .002(4)  -.003(4)
  C8D  .042(5)  .035(5)  .052(5)  -.002(4)  .006(4)  .011(4)
  C9D  .034(4)  .025(4)  .040(4)  -.001(4)  .004(3)  .008(4)
  O1E  .061(4)  .016(3)  .037(3)  .001(3)  .009(3)  .000(3)
  O2E  .048(4)  .028(4)  .044(3)  -.004(3)  .008(3)  -.015(3)
  O3E  .072(5)  .046(4)  .062(4)  .016(4)  .015(3)  .025(4)
  N1E  .040(4)  .019(4)  .035(4)  .006(4)  .007(3)  .003(3)
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
  O1A C1A . 1.219(10) yes
  O2A C1A . 1.271(9) yes
  O2A HO2A . 1.0042 ?
  N1A C2A . 1.494(6) yes
  N1A H1A .  .9100 ?
  N1A H2A .  .9100 ?
  N1A H3A .  .9100 ?
  C1A C2A . 1.538(7) ?
  C2A C3A . 1.527(7) ?
  C2A H21A . 1.0000 ?
  C3A C4A . 1.515(6) ?
  C3A H31A .  .9900 ?
  C3A H32A .  .9900 ?
  C4A C9A . 1.389(7) ?
  C4A C5A . 1.395(6) ?
  C5A C6A . 1.388(6) ?
  C5A H51A .  .9500 ?
  C6A C7A . 1.380(8) ?
  C6A H61A .  .9500 ?
  C7A C8A . 1.388(6) ?
  C7A H71A .  .9500 ?
  C8A C9A . 1.396(6) ?
  C8A H81A .  .9500 ?
  C9A H91A .  .9500 ?
  O1B C1B . 1.247(10) yes
  O2B C1B . 1.265(9) yes
  N1B C2B . 1.490(6) yes
  N1B H1B .  .9100 ?
  N1B H2B .  .9100 ?
  N1B H3B .  .9100 ?
  C1B C2B . 1.538(7) ?
  C2B C3B . 1.521(7) ?
  C2B H21B . 1.0000 ?
  C3B C4B . 1.515(6) ?
  C3B H31B .  .9900 ?
  C3B H32B .  .9900 ?
  C4B C9B . 1.389(7) ?
  C4B C5B . 1.396(6) ?
  C5B C6B . 1.389(6) ?
  C5B H51B .  .9500 ?
  C6B C7B . 1.379(8) ?
  C6B H61B .  .9500 ?
  C7B C8B . 1.389(6) ?
  C7B H71B .  .9500 ?
  C8B C9B . 1.395(6) ?
  C8B H81B .  .9500 ?
  C9B H91B .  .9500 ?
  O1C C1C . 1.298(10) yes
  O2C C1C . 1.230(9) yes
  N1C C2C . 1.489(6) yes
  N1C H1C .  .9100 ?
  N1C H2C .  .9100 ?
  N1C H3C .  .9100 ?
  C1C C2C . 1.534(7) ?
  C2C C3C . 1.523(7) ?
  C2C H21C . 1.0000 ?
  C3C C4C . 1.516(6) ?
  C3C H31C .  .9900 ?
  C3C H32C .  .9900 ?
  C4C C9C . 1.389(7) ?
  C4C C5C . 1.397(6) ?
  C5C C6C . 1.389(6) ?
  C5C H51C .  .9500 ?
  C6C C7C . 1.380(8) ?
  C6C H61C .  .9500 ?
  C7C C8C . 1.390(6) ?
  C7C H71C .  .9500 ?
  C8C C9C . 1.396(6) ?
  C8C H81C .  .9500 ?
  C9C H91C .  .9500 ?
  O1D C1D . 1.261(10) yes
  O2D C1D . 1.250(10) yes
  N1D C2D . 1.491(6) yes
  N1D H1D .  .9100 ?
  N1D H2D .  .9100 ?
  N1D H3D .  .9100 ?
  C1D C2D . 1.535(6) ?
  C2D C3D . 1.516(7) ?
  C2D H21D . 1.0000 ?
  C3D C4D . 1.514(6) ?
  C3D H31D .  .9900 ?
  C3D H32D .  .9900 ?
  C4D C9D . 1.390(7) ?
  C4D C5D . 1.396(6) ?
  C5D C6D . 1.389(6) ?
  C5D H51D .  .9500 ?
  C6D C7D . 1.381(8) ?
  C6D H61D .  .9500 ?
  C7D C8D . 1.388(6) ?
  C7D H71D .  .9500 ?
  C8D C9D . 1.394(6) ?
  C8D H81D .  .9500 ?
  C9D H91D .  .9500 ?
  O1E N1E . 1.243(9) ?
  O2E N1E . 1.272(11) ?
  O3E N1E . 1.230(12) ?