#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200865.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_2200865
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2002
_journal_volume  58
_journal_page_first  o74
_journal_page_last  o76
_publ_section_title
;
Bis(L-proline) hydrogen(1+) perchlorate
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_[local]_cod_cif_authors_sg_H-M  'P 21'
loop_
_publ_author_name
  'S. Pandiarajan'
  'B. Sridhar'
  'R. K. Rajaram'
_chemical_name_common  'Bis(L-proline) H + perchlorate'
_chemical_formula_moiety  '2C5 H9 N O2, H 1+. Cl O4 1-'
_chemical_formula_sum  'C10 H19 Cl N2 O8'
_chemical_formula_iupac  '2C5 H9 N O2, H 1+. Cl O4 1-'
_chemical_formula_weight  330.72
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  7.848(6)
_cell_length_b  7.3951(14)
_cell_length_c  12.834(5)
_cell_angle_alpha  90.00
_cell_angle_beta  90.95(4)
_cell_angle_gamma  90.00
_cell_volume  744.7(5)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.475
_exptl_crystal_density_meas  1.472
_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
  Cl1  .25414(18)  .3333(2)  .78695(10)  .0558(4) Uani d . 1 . . Cl
  O1  .1316(7)  .1989(8)  .8086(4)  .0846(16) Uani d . 1 . . O
  O2  .2853(9)  .4403(12)  .8744(5)  .117(2) Uani d . 1 . . O
  O3  .1820(12)  .4414(14)  .7083(5)  .155(4) Uani d . 1 . . O
  O4  .4024(8)  .2560(12)  .7501(7)  .143(3) Uani d . 1 . . O
  O1A  .3298(5)  .4238(5)  .4672(3)  .0534(11) Uani d . 1 . . O
  O1B  .2380(5)  .5672(5)  .3241(3)  .0503(10) Uani d . 1 . . O
  C11  .2930(6)  .5605(8)  .4187(4)  .0383(11) Uani d . 1 . . C
  O2A  .3390(8)  .1049(8)  .2919(5)  .104(2) Uani d . 1 . . O
  O2B  .1743(7)  .3035(6)  .2113(4)  .0757(15) Uani d . 1 . . O
  H2B  .229(10)  .402(15)  .281(6)  .114 Uiso d . 1 . . H
  C21  .2427(7)  .1478(8)  .2243(4)  .0465(13) Uani d . 1 B . C
  C12  .3080(7)  .7429(8)  .4713(4)  .0405(12) Uani d . 1 A . C
  H12  .3842  .8199  .4309  .049 Uiso calc R 1 . . H
  C13  .1430(8)  .8433(11)  .4895(5)  .0701(19) Uani d D 1 . . C
  H13A  .1112  .9152  .4290  .084 Uiso calc PR  .76(2) A 1 H
  H13B  .0514  .7595  .5041  .084 Uiso calc PR  .76(2) A 1 H
  H13C  .0492  .7738  .4620  .084 Uiso d PR  .24(2) A 2 H
  H13D  .1442  .9580  .4544  .084 Uiso d PR  .24(2) A 2 H
  C14  .1797(14)  .9616(15)  .5814(6)  .064(4) Uani d PDU  .76(2) A 1 C
  H14A  .0754  .9939  .6164  .077 Uiso calc PR  .76(2) A 1 H
  H14B  .2376 1.0713  .5605  .077 Uiso calc PR  .76(2) A 1 H
  C14'  .1192(16)  .857(5)  .6027(8)  .064(9) Uani d PDU  .24(2) A 2 C
  H14C  .0494  .7578  .6273  .077 Uiso calc PR  .24(2) A 2 H
  H14D  .0641  .9700  .6202  .077 Uiso calc PR  .24(2) A 2 H
  C15  .2924(8)  .8481(11)  .6506(4)  .0610(16) Uani d D 1 . . C
  H15A  .2252  .7825  .7009  .073 Uiso calc PR  .76(2) A 1 H
  H15B  .3743  .9232  .6880  .073 Uiso calc PR  .76(2) A 1 H
  H15C  .2843  .7986  .7195  .073 Uiso d PR  .24(2) A 2 H
  H15D  .3517  .9616  .6544  .073 Uiso d PR  .24(2) A 2 H
  N11  .3818(5)  .7193(6)  .5794(3)  .0455(11) Uani d . 1 A . N
  H11A  .3666  .6048  .6011  .055 Uiso calc R 1 . . H
  H11B  .4943  .7429  .5796  .055 Uiso calc R 1 . . H
  C22  .1845(8)  .0128(8)  .1437(5)  .0515(15) Uani d D 1 . . C
  H22  .0609  .0174  .1322  .062 Uiso calc PR  .72(3) B 1 H
  H22'  .0613  .0065  .1544  .062 Uiso d PR  .28(3) B 2 H
  C23  .2814(18)  .0425(14)  .0419(7)  .069(4) Uiso d PD  .72(3) B 1 C
  H23A  .2293  .1380  .0005  .083 Uiso calc PR  .72(3) B 1 H
  H23B  .3998  .0730  .0560  .083 Uiso calc PR  .72(3) B 1 H
  C23'  .183(5)  .034(3)  .0271(8)  .069(10) Uiso d PD  .28(3) B 2 C
  H23C  .2465  .1399  .0066  .083 Uiso calc PR  .28(3) B 2 H
  H23D  .0668  .0446  .0002  .083 Uiso calc PR  .28(3) B 2 H
  C24  .2662(15)  -.1378(11)  -.0128(5)  .104(3) Uani d D 1 . . C
  H24A  .1627  -.1428  -.0550  .125 Uiso calc PR  .72(3) B 1 H
  H24B  .3630  -.1578  -.0574  .125 Uiso calc PR  .72(3) B 1 H
  H24C  .1960  -.1778  -.0712  .125 Uiso d PR  .28(3) B 2 H
  H24D  .3818  -.1218  -.0369  .125 Uiso d PR  .28(3) B 2 H
  C25  .2621(12)  -.2753(10)  .0714(5)  .075(2) Uani d . 1 B . C
  H25A  .3667  -.3451  .0731  .090 Uiso calc R 1 . . H
  H25B  .1668  -.3572  .0608  .090 Uiso calc R 1 . . H
  N21  .2428(7)  -.1712(8)  .1701(3)  .0601(13) Uani d . 1 B . N
  H21A  .1663  -.2258  .2111  .072 Uiso calc R 1 . . H
  H21B  .3432  -.1662  .2049  .072 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
  Cl1  .0636(8)  .0499(8)  .0541(7)  -.0035(8)  .0036(6)  -.0007(8)
  O1  .092(3)  .074(4)  .087(3)  -.017(3)  .005(3)  .013(3)
  O2  .147(6)  .117(6)  .086(4)  -.019(5)  -.006(4)  -.051(4)
  O3  .225(9)  .131(7)  .107(5)  -.042(7)  -.054(5)  .059(5)
  O4  .075(3)  .129(6)  .228(8)  -.010(4)  .037(4)  -.087(6)
  O1A  .074(3)  .034(2)  .053(2)  .007(2)  -.0083(19)  .002(2)
  O1B  .077(3)  .0305(19)  .0426(19)  -.001(2)  -.0133(18)  -.0051(17)
  C11  .037(2)  .033(3)  .044(3)  .000(2)  -.004(2)  .000(2)
  O2A  .133(5)  .070(4)  .106(4)  .040(4)  -.079(4)  -.042(3)
  O2B  .119(4)  .037(3)  .069(3)  .015(3)  -.033(3)  -.012(2)
  C21  .052(3)  .041(3)  .047(3)  -.002(3)  -.009(3)  .002(3)
  C12  .047(3)  .034(3)  .039(3)  -.001(2)  -.010(2)  -.003(2)
  C13  .067(4)  .062(4)  .081(4)  .029(4)  -.024(3)  -.022(4)
  C14  .068(6)  .058(6)  .065(6)  .013(5)  -.003(5)  -.010(5)
  C14'  .041(12)  .056(19)  .095(18)  .000(13)  .023(11)  .033(16)
  C15  .074(4)  .065(4)  .045(3)  .012(4)  .006(3)  -.010(4)
  N11  .048(2)  .041(3)  .048(2)  .001(2)  -.0103(19)  -.006(2)
  C22  .055(3)  .037(3)  .062(4)  .004(3)  -.012(3)  -.009(3)
  C24  .194(10)  .067(6)  .053(4)  .013(6)  .010(5)  .004(4)
  C25  .111(6)  .054(5)  .061(4)  .014(5)  -.003(4)  -.014(4)
  N21  .097(4)  .038(2)  .045(2)  .003(4)  .002(2)  .007(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
  Cl1 O4 . 1.386(6) ?
  Cl1 O2 . 1.391(6) ?
  Cl1 O3 . 1.400(7) ?
  Cl1 O1 . 1.414(6) ?
  O1A C11 . 1.219(7) yes
  O1B C11 . 1.283(6) yes
  O1B H2B . 1.34(11) ?
  C11 C12 . 1.512(7) ?
  O2A C21 . 1.184(7) yes
  O2B C21 . 1.280(8) yes
  O2B H2B . 1.23(10) ?
  C21 C22 . 1.503(8) ?
  C12 C13 . 1.515(8) ?
  C12 N11 . 1.504(7) ?
  C12 H12 .  .98 ?
  C13 C14' . 1.472(10) ?
  C13 C14 . 1.493(8) ?
  C13 H13A .  .97 ?
  C13 H13B .  .97 ?
  C13 H13C .  .96 ?
  C13 H13D .  .96 ?
  C14 C15 . 1.500(8) ?
  C14 H14A .  .97 ?
  C14 H14B .  .97 ?
  C14' C15 . 1.484(10) ?
  C14' H14C .  .97 ?
  C14' H14D .  .97 ?
  C15 N11 . 1.502(8) ?
  C15 H15A .  .97 ?
  C15 H15B .  .97 ?
  C15 H15C .  .96 ?
  C15 H15D .  .96 ?
  N11 H11A .  .90 ?
  N11 H11B .  .90 ?
  C22 N21 . 1.473(8) ?
  C22 C23' . 1.504(11) ?
  C22 C23 . 1.539(9) ?
  C22 H22 .  .98 ?
  C22 H22' .  .98 ?
  C23 C24 . 1.510(9) ?
  C23 H23A .  .97 ?
  C23 H23B .  .97 ?
  C23' C24 . 1.522(11) ?
  C23' H23C .  .97 ?
  C23' H23D .  .97 ?
  C24 C25 . 1.484(11) ?
  C24 H24A .  .97 ?
  C24 H24B .  .97 ?
  C24 H24C .  .97 ?
  C24 H24D .  .97 ?
  C25 N21 . 1.493(8) ?
  C25 H25A .  .97 ?
  C25 H25B .  .97 ?
  N21 H21A .  .90 ?
  N21 H21B .  .90 ?