#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200690.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_2200690
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o1078
_journal_page_last  o1080
_publ_section_title
;
DL-Phenylalaninium dihydrogen phosphate
;
loop_
_publ_author_name
  'B. Ravikumar'
  'B. Sridhar'
  'R. K. Rajaram'
_chemical_name_common  'DL-phenylalaninium dihydrogen phosphate'
_chemical_formula_moiety  'C9 H12 N O2 1+, H2 P O4 1-'
_chemical_formula_sum  'C9 H14 N O6 P'
_chemical_formula_iupac  'C9 H12 N O2 1+, H2 P O4 1-'
_chemical_formula_weight  263.18
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x, -y, z+1/2'
_cell_length_a  13.899(7)
_cell_length_b  9.956(8)
_cell_length_c  9.051(2)
_cell_angle_alpha  90.00
_cell_angle_beta  108.726(8)
_cell_angle_gamma  90.00
_cell_volume  1186.1(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.474
_exptl_crystal_density_meas  1.469
_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
  P1  .15371(6)  .54460(7)  .41704(8)  .0278(2) Uani d . 1 . . P
  O11  .10420(19)  .4143(2)  .3594(3)  .0396(6) Uani d . 1 . . O
  O12  .20465(19)  .6095(2)  .3097(3)  .0356(6) Uani d . 1 . . O
  O13  .07248(19)  .6420(2)  .4400(3)  .0392(6) Uani d . 1 . . O
  H13  .0930  .7195  .4434  .059 Uiso calc R 1 . . H
  O14  .23888(18)  .5305(2)  .5782(3)  .0404(6) Uani d . 1 . . O
  H14  .2268  .4654  .6249  .061 Uiso calc R 1 . . H
  P2  .88507(6)  -.02763(8)  .13941(8)  .0295(2) Uani d . 1 . . P
  O21  .93679(19)  .0995(2)  .2073(3)  .0392(6) Uani d . 1 . . O
  O22  .8397(2)  -.1064(2)  .2453(3)  .0367(6) Uani d . 1 . . O
  O23  .96464(19)  -.1190(2)  .0969(3)  .0410(6) Uani d . 1 . . O
  H23  .9463  -.1976  .0923  .061 Uiso calc R 1 . . H
  O24  .79616(17)  -.0018(3)  -.0140(3)  .0437(6) Uani d . 1 . . O
  H24  .8192  .0215  -.0829  .066 Uiso calc R 1 . . H
  O1A  .1404(2)  -.1116(2)  .4569(3)  .0389(6) Uani d . 1 . . O
  O1B  .21052(19)  -.1453(2)  .2699(3)  .0365(6) Uani d . 1 . . O
  H1B  .202(5)  -.264(7)  .296(8)  .12(2) Uiso d . 1 . . H
  C11  .1743(3)  -.0704(3)  .3562(4)  .0285(7) Uani d . 1 . . C
  C12  .1726(2)  .0786(3)  .3202(4)  .0292(7) Uani d . 1 . . C
  H12  .1255  .0909  .2142  .035 Uiso calc R 1 . . H
  N11  .1282(2)  .1489(3)  .4269(3)  .0317(6) Uani d . 1 . . N
  H11A  .1258  .2367  .4075  .048 Uiso calc R 1 . . H
  H11B  .1664  .1340  .5252  .048 Uiso calc R 1 . . H
  H11C  .0656  .1183  .4122  .048 Uiso calc R 1 . . H
  C13  .2747(3)  .1381(3)  .3228(4)  .0382(7) Uani d . 1 . . C
  H13A  .2966  .0921  .2446  .046 Uiso calc R 1 . . H
  H13B  .2641  .2316  .2920  .046 Uiso calc R 1 . . H
  C14  .3596(3)  .1310(3)  .4755(4)  .0364(7) Uani d . 1 . . C
  C15  .3791(3)  .2374(4)  .5789(5)  .0545(10) Uani d . 1 . . C
  H15  .3356  .3110  .5580  .065 Uiso calc R 1 . . H
  C16  .4620(5)  .2360(7)  .7124(6)  .0870(17) Uani d . 1 . . C
  H16  .4740  .3078  .7817  .104 Uiso calc R 1 . . H
  C17  .5268(5)  .1278(9)  .7427(7)  .103(3) Uani d . 1 . . C
  H17  .5839  .1270  .8314  .124 Uiso calc R 1 . . H
  C18  .5072(4)  .0215(7)  .6422(9)  .094(2) Uani d . 1 . . C
  H18  .5505  -.0523  .6634  .112 Uiso calc R 1 . . H
  C19  .4244(3)  .0228(4)  .5110(6)  .0628(11) Uani d . 1 . . C
  H19  .4115  -.0509  .4443  .075 Uiso calc R 1 . . H
  O2A  .90648(19)  .6226(2)  .0761(3)  .0365(6) Uani d . 1 . . O
  O2B  .82341(19)  .6439(2)  .2493(3)  .0380(6) Uani d . 1 . . O
  H2B  .830(5)  .765(6)  .243(8)  .103(19) Uiso d . 1 . . H
  C21  .8626(2)  .5756(3)  .1621(4)  .0286(7) Uani d . 1 . . C
  C22  .8505(2)  .4243(3)  .1712(4)  .0292(7) Uani d . 1 . . C
  H22  .8623  .3989  .2802  .035 Uiso calc R 1 . . H
  N21  .9282(2)  .3595(3)  .1158(3)  .0329(6) Uani d . 1 . . N
  H21A  .9227  .2707  .1208  .049 Uiso calc R 1 . . H
  H21B  .9897  .3850  .1757  .049 Uiso calc R 1 . . H
  H21C  .9189  .3838  .0176  .049 Uiso calc R 1 . . H
  C23  .7446(3)  .3759(3)  .0726(4)  .0375(7) Uani d . 1 . . C
  H23A  .7176  .4382  -.0131  .045 Uiso calc R 1 . . H
  H23B  .7516  .2893  .0280  .045 Uiso calc R 1 . . H
  C24  .6682(2)  .3623(3)  .1593(4)  .0326(7) Uani d . 1 . . C
  C25  .6898(3)  .2830(3)  .2909(4)  .0505(9) Uani d . 1 . . C
  H25  .7535  .2430  .3299  .061 Uiso calc R 1 . . H
  C26  .6198(3)  .2618(3)  .3653(4)  .0745(15) Uani d R 1 . . C
  H26  .6366  .2098  .4553  .089 Uiso calc R 1 . . H
  C27  .5265(5)  .3161(6)  .3085(8)  .089(2) Uani d . 1 . . C
  H27  .4787  .2998  .3584  .107 Uiso calc R 1 . . H
  C28  .5011(3)  .3956(6)  .1773(9)  .087(2) Uani d . 1 . . C
  H28  .4365  .4328  .1386  .105 Uiso calc R 1 . . H
  C29  .5739(3)  .4204(4)  .1013(6)  .0576(10) Uani d . 1 . . C
  H29  .5581  .4752  .0135  .069 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
  P1  .0372(4)  .0215(3)  .0274(4)  -.0028(3)  .0140(3)  .0003(3)
  O11  .0556(15)  .0228(11)  .0404(14)  -.0039(11)  .0154(12)  .0007(10)
  O12  .0554(16)  .0258(11)  .0343(13)  -.0016(10)  .0265(12)  -.0004(9)
  O13  .0440(13)  .0299(12)  .0507(15)  -.0007(10)  .0248(12)  -.0011(11)
  O14  .0421(13)  .0456(15)  .0319(13)  -.0092(10)  .0095(11)  .0077(10)
  P2  .0402(4)  .0247(4)  .0253(4)  -.0039(3)  .0129(3)  -.0006(3)
  O21  .0527(15)  .0283(11)  .0341(13)  -.0074(10)  .0104(11)  .0000(10)
  O22  .0608(15)  .0270(11)  .0312(12)  -.0059(11)  .0272(12)  -.0036(10)
  O23  .0516(15)  .0323(11)  .0473(15)  -.0060(11)  .0274(12)  -.0024(11)
  O24  .0432(13)  .0555(14)  .0308(13)  -.0069(12)  .0096(11)  .0036(12)
  O1A  .0721(17)  .0246(11)  .0285(13)  -.0016(11)  .0282(12)  -.0007(10)
  O1B  .0587(15)  .0282(11)  .0306(12)  .0011(10)  .0257(11)  .0009(9)
  C11  .0388(18)  .0254(15)  .0218(15)  -.0051(13)  .0105(13)  .0003(13)
  C12  .0392(16)  .0261(15)  .0239(15)  -.0029(13)  .0124(13)  -.0003(13)
  N11  .0429(16)  .0226(12)  .0300(15)  -.0022(11)  .0124(12)  .0015(11)
  C13  .0528(19)  .0318(16)  .0333(17)  -.0051(14)  .0182(15)  .0016(13)
  C14  .0407(17)  .0363(16)  .0372(18)  -.0033(14)  .0194(15)  .0024(14)
  C15  .060(2)  .055(2)  .048(2)  -.0107(18)  .0160(19)  -.0118(18)
  C16  .092(4)  .103(4)  .055(3)  -.039(4)  .009(3)  -.014(3)
  C17  .071(3)  .150(7)  .066(4)  -.037(4)  -.010(3)  .040(4)
  C18  .060(3)  .098(4)  .114(5)  .019(3)  .015(3)  .053(4)
  C19  .060(2)  .056(3)  .073(3)  .012(2)  .022(2)  .012(2)
  O2A  .0545(14)  .0277(12)  .0356(14)  -.0014(10)  .0260(12)  -.0002(10)
  O2B  .0548(14)  .0293(12)  .0403(13)  .0005(10)  .0296(12)  -.0039(10)
  C21  .0316(16)  .0280(15)  .0256(16)  .0026(13)  .0083(13)  .0009(13)
  C22  .0371(16)  .0268(16)  .0259(16)  .0004(13)  .0132(14)  .0009(13)
  N21  .0418(15)  .0240(13)  .0383(15)  -.0015(11)  .0207(13)  .0013(11)
  C23  .0405(17)  .0426(18)  .0298(17)  -.0071(14)  .0119(14)  -.0048(14)
  C24  .0352(15)  .0305(14)  .0327(16)  -.0052(12)  .0117(13)  -.0054(13)
  C25  .055(2)  .051(2)  .045(2)  -.0188(17)  .0148(17)  .0059(17)
  C26  .099(4)  .082(3)  .056(3)  -.047(3)  .045(3)  -.010(2)
  C27  .100(4)  .084(4)  .119(5)  -.045(3)  .086(4)  -.037(4)
  C28  .042(2)  .071(3)  .158(6)  -.002(2)  .045(3)  -.029(4)
  C29  .046(2)  .052(2)  .075(3)  .0061(18)  .020(2)  .003(2)
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
  P1 O11 . 1.483(3) yes
  P1 O12 . 1.518(2) yes
  P1 O13 . 1.552(3) yes
  P1 O14 . 1.562(3) yes
  O13 H13 .  .8200 ?
  O14 H14 .  .8200 ?
  P2 O21 . 1.488(3) yes
  P2 O22 . 1.523(2) yes
  P2 O24 . 1.556(3) yes
  P2 O23 . 1.572(3) yes
  O23 H23 .  .8200 ?
  O24 H24 .  .8200 ?
  O1A C11 . 1.224(4) yes
  O1B C11 . 1.293(4) yes
  O1B H1B . 1.22(7) ?
  C11 C12 . 1.518(4) ?
  C12 N11 . 1.479(4) ?
  C12 C13 . 1.531(5) ?
  C12 H12 .  .9800 ?
  N11 H11A .  .8900 ?
  N11 H11B .  .8900 ?
  N11 H11C .  .8900 ?
  C13 C14 . 1.503(5) ?
  C13 H13A .  .9700 ?
  C13 H13B .  .9700 ?
  C14 C19 . 1.374(5) ?
  C14 C15 . 1.382(5) ?
  C15 C16 . 1.376(7) ?
  C15 H15 .  .9300 ?
  C16 C17 . 1.375(10) ?
  C16 H16 .  .9300 ?
  C17 C18 . 1.365(11) ?
  C17 H17 .  .9300 ?
  C18 C19 . 1.362(7) ?
  C18 H18 .  .9300 ?
  C19 H19 .  .9300 ?
  O2A C21 . 1.226(4) yes
  O2B C21 . 1.287(4) yes
  O2B H2B . 1.21(6) ?
  C21 C22 . 1.521(4) ?
  C22 N21 . 1.477(4) ?
  C22 C23 . 1.533(4) ?
  C22 H22 .  .9800 ?
  N21 H21A .  .8900 ?
  N21 H21B .  .8900 ?
  N21 H21C .  .8900 ?
  C23 C24 . 1.515(4) ?
  C23 H23A .  .9700 ?
  C23 H23B .  .9700 ?
  C24 C29 . 1.374(5) ?
  C24 C25 . 1.379(5) ?
  C25 C26 . 1.3659 ?
  C25 H25 .  .9300 ?
  C26 C27 . 1.346(8) ?
  C26 H26 .  .9300 ?
  C27 C28 . 1.375(9) ?
  C27 H27 .  .9300 ?
  C28 C29 . 1.415(7) ?
  C28 H28 .  .9300 ?
  C29 H29 .  .9300 ?