#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200870.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_2200870
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2002
_journal_volume  58
_journal_page_first  o95
_journal_page_last  o97
_publ_section_title
;
DL-Valinium nitrate
;
loop_
_publ_author_name
  'Srinivasan, N.'
  'Sridhar, B.'
  'Rajaram, R. K.'
_chemical_name_common  'DL-valinium nitrate'
_chemical_formula_moiety  'C5 H12 N O2 1+, NO3 1-'
_chemical_formula_sum  'C5 H12 N2 O5'
_chemical_formula_iupac  'C5 H12 N O2 1+, NO3 1-'
_chemical_formula_weight  180.17
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.5695(10)
_cell_length_b  11.2104(16)
_cell_length_c  17.537(3)
_cell_angle_alpha  108.52(3)
_cell_angle_beta  104.14(2)
_cell_angle_gamma  90.25(2)
_cell_volume  1722.9(4)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.389
_exptl_crystal_density_meas  1.375
_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
  N1  .1736(3)  .6748(3)  .51090(16)  .0383(6) Uani d . 1 . . N
  O1A  .1612(3)  .6144(3)  .55649(16)  .0536(7) Uani d . 1 . . O
  O1B  .1719(3)  .6211(2)  .43638(14)  .0524(7) Uani d . 1 . . O
  O1C  .1884(3)  .7944(2)  .53753(14)  .0498(6) Uani d . 1 . . O
  N2  .1416(3)  .1749(3)  .50931(16)  .0397(6) Uani d . 1 . . N
  O2A  .1516(3)  .1128(3)  .55619(17)  .0629(8) Uani d . 1 . . O
  O2B  .1337(3)  .1246(2)  .43381(15)  .0554(7) Uani d . 1 . . O
  O2C  .1368(3)  .2936(2)  .53592(14)  .0489(6) Uani d . 1 . . O
  N3  .1704(3)  .3332(3)  .01105(17)  .0397(6) Uani d . 1 . . N
  O3A  .1595(3)  .4387(2)  .05717(16)  .0547(7) Uani d . 1 . . O
  O3B  .1713(3)  .3136(2)  -.06314(15)  .0569(7) Uani d . 1 . . O
  O3C  .1811(3)  .2391(2)  .03680(14)  .0482(6) Uani d . 1 . . O
  N4  .8549(3)  .1627(3)  -.00921(16)  .0382(6) Uani d . 1 . . N
  O4A  .8463(3)  .0542(2)  -.05549(17)  .0622(8) Uani d . 1 . . O
  O4B  .8636(3)  .1893(2)  .06651(14)  .0531(7) Uani d . 1 . . O
  O4C  .8580(3)  .2546(2)  -.03675(14)  .0507(6) Uani d . 1 . . O
  O11  .8927(3) 1.1682(2)  .25717(14)  .0470(6) Uani d . 1 . . O
  O12  .7869(3) 1.0479(3)  .31090(14)  .0619(8) Uani d . 1 . . O
  H12  .8094 1.1098  .3533  .093 Uiso calc R 1 . . H
  C11  .8311(3) 1.0710(3)  .25139(18)  .0359(7) Uani d . 1 . . C
  C12  .7917(3)  .9582(3)  .17196(18)  .0333(7) Uani d . 1 . . C
  H12A  .8145  .8819  .1866  .040 Uiso calc R 1 . . H
  N11  .8853(3)  .9727(2)  .11845(15)  .0344(6) Uani d . 1 . . N
  H11A  .8642  .9077  .0712  .052 Uiso calc R 1 . . H
  H11B  .9778  .9749  .1451  .052 Uiso calc R 1 . . H
  H11C  .8700 1.0442  .1071  .052 Uiso calc R 1 . . H
  C13  .6305(4)  .9430(3)  .1256(2)  .0463(8) Uani d . 1 . . C
  H13  .6212  .8848  .0691  .056 Uiso calc R 1 . . H
  C14  .5402(5)  .8813(5)  .1654(3)  .0739(13) Uani d . 1 . . C
  H14A  .5795  .8044  .1700  .111 Uiso calc R 1 . . H
  H14B  .4423  .8626  .1315  .111 Uiso calc R 1 . . H
  H14C  .5417  .9378  .2198  .111 Uiso calc R 1 . . H
  C15  .5736(5) 1.0651(5)  .1170(3)  .0711(12) Uani d . 1 . . C
  H15A  .6333 1.1015  .0919  .107 Uiso calc R 1 . . H
  H15B  .5753 1.1230  .1710  .107 Uiso calc R 1 . . H
  H15C  .4761 1.0482  .0826  .107 Uiso calc R 1 . . H
  O21  .1042(3)  .9136(2)  .24535(14)  .0468(6) Uani d . 1 . . O
  O22  .2003(3)  .7362(3)  .18907(14)  .0593(8) Uani d . 1 . . O
  H22  .1754  .7553  .1466  .089 Uiso calc R 1 . . H
  C21  .1632(3)  .8214(3)  .25036(18)  .0351(7) Uani d . 1 . . C
  C22  .2082(3)  .7892(3)  .33035(18)  .0351(7) Uani d . 1 . . C
  H22A  .1868  .6981  .3167  .042 Uiso calc R 1 . . H
  N21  .1160(3)  .8569(2)  .38509(15)  .0349(6) Uani d . 1 . . N
  H21A  .1394  .8401  .4327  .052 Uiso calc R 1 . . H
  H21B  .0233  .8312  .3595  .052 Uiso calc R 1 . . H
  H21C  .1304  .9397  .3956  .052 Uiso calc R 1 . . H
  C23  .3694(4)  .8233(4)  .3754(2)  .0460(8) Uani d . 1 . . C
  H23  .3813  .8205  .4319  .055 Uiso calc R 1 . . H
  C24  .4604(5)  .7251(5)  .3340(3)  .0750(14) Uani d . 1 . . C
  H24A  .4234  .6425  .3291  .112 Uiso calc R 1 . . H
  H24B  .5589  .7418  .3671  .112 Uiso calc R 1 . . H
  H24C  .4566  .7289  .2796  .112 Uiso calc R 1 . . H
  C25  .4237(4)  .9557(4)  .3841(3)  .0658(11) Uani d . 1 . . C
  H25A  .3643 1.0157  .4103  .099 Uiso calc R 1 . . H
  H25B  .4192  .9609  .3299  .099 Uiso calc R 1 . . H
  H25C  .5219  .9744  .4174  .099 Uiso calc R 1 . . H
  O31  .8968(3)  .6711(2)  .25551(14)  .0475(6) Uani d . 1 . . O
  O32  .8201(3)  .5390(2)  .31209(14)  .0573(7) Uani d . 1 . . O
  H32  .8487  .5985  .3554  .086 Uiso calc R 1 . . H
  C31  .8441(3)  .5699(3)  .24979(18)  .0345(7) Uani d . 1 . . C
  C32  .7936(3)  .4635(3)  .16793(17)  .0314(6) Uani d . 1 . . C
  H32A  .8012  .3824  .1780  .038 Uiso calc R 1 . . H
  N31  .8923(3)  .4737(2)  .11565(15)  .0344(6) Uani d . 1 . . N
  H31A  .8658  .4123  .0667  .052 Uiso calc R 1 . . H
  H31B  .9827  .4666  .1414  .052 Uiso calc R 1 . . H
  H31C  .8872  .5483  .1077  .052 Uiso calc R 1 . . H
  C33  .6353(4)  .4736(3)  .1242(2)  .0430(8) Uani d . 1 . . C
  H33  .6268  .5595  .1219  .052 Uiso calc R 1 . . H
  C34  .5349(5)  .4500(6)  .1735(3)  .0844(16) Uani d . 1 . . C
  H34A  .5641  .5082  .2294  .127 Uiso calc R 1 . . H
  H34B  .5393  .3651  .1747  .127 Uiso calc R 1 . . H
  H34C  .4377  .4618  .1478  .127 Uiso calc R 1 . . H
  C35  .5889(4)  .3815(4)  .0358(2)  .0606(11) Uani d . 1 . . C
  H35A  .6527  .3961  .0045  .091 Uiso calc R 1 . . H
  H35B  .4918  .3936  .0101  .091 Uiso calc R 1 . . H
  H35C  .5929  .2965  .0370  .091 Uiso calc R 1 . . H
  O41  .1078(3)  .4142(2)  .24196(14)  .0470(6) Uani d . 1 . . O
  O42  .1884(3)  .2272(3)  .18719(14)  .0566(7) Uani d . 1 . . O
  H42  .1615  .2429  .1436  .085 Uiso calc R 1 . . H
  C41  .1609(3)  .3196(3)  .24838(18)  .0349(7) Uani d . 1 . . C
  C42  .2078(3)  .2956(3)  .33083(17)  .0318(7) Uani d . 1 . . C
  H42A  .2007  .2044  .3209  .038 Uiso calc R 1 . . H
  N41  .1078(3)  .3558(2)  .38156(15)  .0341(6) Uani d . 1 . . N
  H41A  .1331  .3433  .4306  .051 Uiso calc R 1 . . H
  H41B  .0178  .3220  .3550  .051 Uiso calc R 1 . . H
  H41C  .1127  .4384  .3895  .051 Uiso calc R 1 . . H
  C43  .3651(4)  .3510(4)  .3754(2)  .0441(8) Uani d . 1 . . C
  H43  .3716  .4404  .3799  .053 Uiso calc R 1 . . H
  C44  .4689(5)  .2850(6)  .3252(3)  .0845(16) Uani d . 1 . . C
  H44A  .4392  .2900  .2700  .127 Uiso calc R 1 . . H
  H44B  .4678  .1980  .3222  .127 Uiso calc R 1 . . H
  H44C  .5650  .3254  .3519  .127 Uiso calc R 1 . . H
  C45  .4122(4)  .3429(4)  .4625(2)  .0593(10) Uani d . 1 . . C
  H45A  .3469  .3844  .4941  .089 Uiso calc R 1 . . H
  H45B  .5083  .3833  .4892  .089 Uiso calc R 1 . . H
  H45C  .4111  .2558  .4594  .089 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
  N1  .0445(15)  .0408(16)  .0332(15)  .0095(12)  .0112(11)  .0160(12)
  O1A  .0677(17)  .0613(17)  .0492(15)  .0133(13)  .0218(13)  .0368(13)
  O1B  .0895(19)  .0365(13)  .0343(13)  .0090(12)  .0270(12)  .0076(10)
  O1C  .0804(18)  .0363(14)  .0311(12)  .0042(12)  .0161(12)  .0075(10)
  N2  .0472(16)  .0418(16)  .0358(15)  .0136(12)  .0165(12)  .0162(13)
  O2A  .087(2)  .0676(18)  .0550(16)  .0205(15)  .0277(15)  .0412(15)
  O2B  .095(2)  .0382(14)  .0376(14)  .0090(13)  .0312(13)  .0081(10)
  O2C  .0741(17)  .0393(14)  .0322(12)  .0129(12)  .0156(11)  .0086(10)
  N3  .0483(16)  .0375(16)  .0356(15)  .0060(12)  .0143(12)  .0123(12)
  O3A  .0746(18)  .0352(14)  .0520(15)  .0093(12)  .0278(13)  .0027(11)
  O3B  .101(2)  .0456(14)  .0380(14)  .0210(14)  .0335(14)  .0204(11)
  O3C  .0761(17)  .0411(13)  .0318(12)  .0097(12)  .0156(11)  .0164(10)
  N4  .0436(15)  .0382(16)  .0354(15)  .0045(12)  .0150(12)  .0119(12)
  O4A  .090(2)  .0360(14)  .0525(16)  .0062(13)  .0262(15)  -.0026(12)
  O4B  .0886(19)  .0457(14)  .0350(13)  .0162(13)  .0275(12)  .0182(11)
  O4C  .0784(18)  .0453(14)  .0316(12)  .0034(12)  .0147(12)  .0166(10)
  O11  .0607(15)  .0418(14)  .0333(12)  -.0067(12)  .0131(11)  .0049(10)
  O12  .100(2)  .0550(16)  .0260(12)  -.0188(14)  .0251(13)  .0008(11)
  C11  .0423(17)  .0397(19)  .0247(15)  .0016(14)  .0078(13)  .0100(13)
  C12  .0451(18)  .0307(16)  .0264(15)  .0025(13)  .0134(13)  .0095(12)
  N11  .0417(14)  .0354(14)  .0264(13)  .0080(11)  .0117(11)  .0083(11)
  C13  .0431(19)  .054(2)  .0357(18)  .0001(15)  .0122(14)  .0052(15)
  C14  .062(3)  .091(3)  .064(3)  -.022(2)  .019(2)  .017(2)
  C15  .054(2)  .086(3)  .073(3)  .021(2)  .009(2)  .031(2)
  O21  .0608(15)  .0515(15)  .0341(12)  .0209(12)  .0119(11)  .0222(11)
  O22  .096(2)  .0636(17)  .0251(12)  .0341(15)  .0230(12)  .0175(11)
  C21  .0420(17)  .0373(17)  .0257(15)  .0055(14)  .0080(13)  .0106(13)
  C22  .0477(18)  .0340(16)  .0273(15)  .0129(14)  .0125(13)  .0129(12)
  N21  .0452(15)  .0356(14)  .0253(13)  .0063(11)  .0109(11)  .0106(11)
  C23  .0480(19)  .058(2)  .0327(17)  .0141(16)  .0096(14)  .0171(15)
  C24  .063(3)  .097(4)  .068(3)  .040(3)  .022(2)  .027(3)
  C25  .051(2)  .071(3)  .065(3)  -.005(2)  .0113(19)  .011(2)
  O31  .0638(15)  .0398(14)  .0333(12)  -.0064(11)  .0123(11)  .0049(10)
  O32  .094(2)  .0496(15)  .0270(12)  -.0076(14)  .0201(12)  .0073(11)
  C31  .0393(17)  .0400(19)  .0255(15)  .0065(14)  .0091(12)  .0120(13)
  C32  .0403(17)  .0294(15)  .0249(14)  .0031(12)  .0093(12)  .0087(12)
  N31  .0425(14)  .0339(14)  .0265(13)  .0078(11)  .0094(11)  .0090(11)
  C33  .0415(18)  .0401(18)  .0410(18)  .0068(14)  .0084(14)  .0063(14)
  C34  .053(3)  .120(4)  .069(3)  -.002(3)  .023(2)  .011(3)
  C35  .060(2)  .057(2)  .052(2)  .0129(19)  .0000(18)  .0101(18)
  O41  .0615(15)  .0510(15)  .0317(12)  .0209(12)  .0100(11)  .0193(11)
  O42  .0865(19)  .0593(16)  .0250(12)  .0283(14)  .0162(12)  .0136(11)
  C41  .0399(17)  .0360(17)  .0265(15)  .0073(14)  .0071(13)  .0084(13)
  C42  .0421(17)  .0314(16)  .0258(15)  .0119(13)  .0128(12)  .0115(12)
  N41  .0445(15)  .0340(14)  .0252(12)  .0060(11)  .0096(11)  .0113(11)
  C43  .0437(18)  .059(2)  .0350(17)  .0053(16)  .0086(14)  .0236(16)
  C44  .050(2)  .142(5)  .064(3)  .020(3)  .022(2)  .031(3)
  C45  .057(2)  .075(3)  .045(2)  .001(2)  -.0009(17)  .0284(19)
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
  N1 O1A . 1.226(3) yes
  N1 O1B . 1.249(3) yes
  N1 O1C . 1.266(4) yes
  N2 O2A . 1.222(4) yes
  N2 O2B . 1.246(3) yes
  N2 O2C . 1.268(4) yes
  N3 O3A . 1.224(4) yes
  N3 O3B . 1.251(3) yes
  N3 O3C . 1.268(4) yes
  N4 O4A . 1.218(4) yes
  N4 O4B . 1.246(3) yes
  N4 O4C . 1.272(4) yes
  O11 C11 . 1.199(4) yes
  O12 C11 . 1.312(4) yes
  O12 H12 .  .82 ?
  C11 C12 . 1.517(4) ?
  C12 N11 . 1.488(4) ?
  C12 C13 . 1.539(5) ?
  C12 H12A .  .98 ?
  N11 H11A .  .89 ?
  N11 H11B .  .89 ?
  N11 H11C .  .89 ?
  C13 C15 . 1.513(6) ?
  C13 C14 . 1.520(5) ?
  C13 H13 .  .98 ?
  C14 H14A .  .96 ?
  C14 H14B .  .96 ?
  C14 H14C .  .96 ?
  C15 H15A .  .96 ?
  C15 H15B .  .96 ?
  C15 H15C .  .96 ?
  O21 C21 . 1.197(4) yes
  O22 C21 . 1.315(4) yes
  O22 H22 .  .82 ?
  C21 C22 . 1.521(4) ?
  C22 N21 . 1.494(4) ?
  C22 C23 . 1.535(5) ?
  C22 H22A .  .98 ?
  N21 H21A .  .89 ?
  N21 H21B .  .89 ?
  N21 H21C .  .89 ?
  C23 C25 . 1.519(6) ?
  C23 C24 . 1.520(5) ?
  C23 H23 .  .98 ?
  C24 H24A .  .96 ?
  C24 H24B .  .96 ?
  C24 H24C .  .96 ?
  C25 H25A .  .96 ?
  C25 H25B .  .96 ?
  C25 H25C .  .96 ?
  O31 C31 . 1.204(4) yes
  O32 C31 . 1.315(4) yes
  O32 H32 .  .82 ?
  C31 C32 . 1.512(4) ?
  C32 N31 . 1.495(4) ?
  C32 C33 . 1.543(4) ?
  C32 H32A .  .98 ?
  N31 H31A .  .89 ?
  N31 H31B .  .89 ?
  N31 H31C .  .89 ?
  C33 C34 . 1.514(6) ?
  C33 C35 . 1.519(5) ?
  C33 H33 .  .98 ?
  C34 H34A .  .96 ?
  C34 H34B .  .96 ?
  C34 H34C .  .96 ?
  C35 H35A .  .96 ?
  C35 H35B .  .96 ?
  C35 H35C .  .96 ?
  O41 C41 . 1.204(4) yes
  O42 C41 . 1.314(4) yes
  O42 H42 .  .82 ?
  C41 C42 . 1.515(4) ?
  C42 N41 . 1.485(4) ?
  C42 C43 . 1.540(5) ?
  C42 H42A .  .98 ?
  N41 H41A .  .89 ?
  N41 H41B .  .89 ?
  N41 H41C .  .89 ?
  C43 C45 . 1.516(5) ?
  C43 C44 . 1.526(5) ?
  C43 H43 .  .98 ?
  C44 H44A .  .96 ?
  C44 H44B .  .96 ?
  C44 H44C .  .96 ?
  C45 H45A .  .96 ?
  C45 H45B .  .96 ?
  C45 H45C .  .96 ?