#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012829.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_2012829
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  m418
_journal_page_last  m420
_publ_section_title
;
Losartan potassium, a non-peptide agent for the treatment of arterial
hypertension
;
loop_
_publ_author_name
  'Fern\'andez, Daniel'
  'Vega, Daniel'
  'Ellena, Javier A.'
  'Echeverr\'ia, Gustavo'
_chemical_formula_moiety  'K + , C22 H22 Cl N6 O -'
_chemical_formula_sum  'C22 H22 Cl K N6 O'
_chemical_formula_iupac  'K (C22 H22 Cl N6 O)'
_chemical_formula_weight  461.01
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  15.5724(3)
_cell_length_b  7.4976(2)
_cell_length_c  24.2640(5)
_cell_angle_alpha  90
_cell_angle_beta  128.4980(10)
_cell_angle_gamma  90
_cell_volume  2217.16(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.381
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
  K -0.03166(4) 0.25891(6) -0.07829(2) 0.03292(15) Uani d . 1 . 1 K
  Cl1 0.54908(11) 0.3801(2) 0.33591(6) 0.0641(4) Uani d P 0.7 . 1 Cl
  O1 0.25211(11) 0.6667(2) 0.17577(8) 0.0381(4) Uani d . 1 . 1 O
  H1 0.3035 0.7395 0.2015 0.057 Uiso calc R 1 . 1 H
  N1 0.01100(15) -0.3752(2) -0.08435(10) 0.0387(4) Uani d . 1 . 1 N
  N2 -0.04356(15) -0.3117(3) -0.06134(10) 0.0416(5) Uani d . 1 . 1 N
  N3 -0.07054(15) -0.1437(3) -0.08049(10) 0.0382(4) Uani d . 1 . 1 N
  N4 -0.03420(15) -0.0924(2) -0.11621(10) 0.0368(4) Uani d . 1 . 1 N
  N5 0.3764(4) 0.4284(8) 0.13590(18) 0.0305(10) Uani d P 0.7 . 1 N
  N6 0.5496(3) 0.3650(5) 0.2261(3) 0.0321(7) Uani d P 0.7 . 1 N
  C1 0.01533(17) -0.2366(3) -0.11699(10) 0.0312(5) Uani d . 1 . 1 C
  C2 0.07333(17) -0.2391(3) -0.14743(11) 0.0353(5) Uani d . 1 . 1 C
  C3 0.04853(19) -0.3729(3) -0.19560(11) 0.0438(6) Uani d . 1 . 1 C
  H3 -0.0038 -0.4619 -0.2073 0.053 Uiso calc R 1 . 1 H
  C4 0.0990(2) -0.3776(4) -0.22638(13) 0.0552(7) Uani d . 1 . 1 C
  H4 0.0816 -0.4695 -0.2588 0.066 Uiso calc R 1 . 1 H
  C5 0.1748(2) -0.2488(4) -0.20992(13) 0.0564(8) Uani d . 1 . 1 C
  H5 0.2093 -0.2514 -0.2313 0.068 Uiso calc R 1 . 1 H
  C6 0.20077(19) -0.1150(4) -0.16209(12) 0.0463(6) Uani d . 1 . 1 C
  H6 0.253 -0.0267 -0.1511 0.056 Uiso calc R 1 . 1 H
  C7 0.15146(17) -0.1079(3) -0.12983(11) 0.0358(5) Uani d . 1 . 1 C
  C8 0.18323(17) 0.0372(3) -0.07845(11) 0.0348(5) Uani d . 1 . 1 C
  C9 0.1899(2) 0.2127(3) -0.09409(13) 0.0463(6) Uani d . 1 . 1 C
  H9 0.1721 0.2395 -0.1384 0.056 Uiso calc R 1 . 1 H
  C10 0.2220(2) 0.3490(3) -0.04642(14) 0.0482(6) Uani d . 1 . 1 C
  H10 0.2262 0.4676 -0.0584 0.058 Uiso d R 1 . 1 H
  C11 0.24775(17) 0.3144(3) 0.01826(12) 0.0398(5) Uani d . 1 . 1 C
  C12 0.24028(17) 0.1400(3) 0.03451(12) 0.0363(5) Uani d . 1 . 1 C
  H12 0.2564 0.1146 0.0784 0.044 Uiso calc R 1 . 1 H
  C13 0.20965(16) 0.0037(3) -0.01275(11) 0.0338(5) Uani d . 1 . 1 C
  H13 0.2065 -0.115 -0.0004 0.041 Uiso calc R 1 . 1 H
  C14 0.28056(19) 0.4642(3) 0.06942(13) 0.0483(6) Uani d . 1 . 1 C
  H14A 0.2838 0.5798 0.051 0.058 Uiso d R 1 . 1 H
  H14B 0.2228 0.4735 0.0749 0.058 Uiso d R 1 . 1 H
  C15 0.3845(6) 0.4350(10) 0.1961(3) 0.0312(13) Uani d P 0.7 . 1 C
  C16 0.2923(10) 0.4911(17) 0.1973(7) 0.0386(14) Uani d P 0.7 . 1 C
  H16A 0.2296 0.4113 0.1642 0.046 Uiso d PR 0.7 . 1 H
  H16B 0.3153 0.4691 0.2451 0.046 Uiso d PR 0.7 . 1 H
  C17 0.4891(3) 0.3947(5) 0.2486(2) 0.0334(8) Uani d P 0.7 . 1 C
  C18 0.4782(4) 0.3871(7) 0.1564(3) 0.0367(11) Uani d P 0.7 . 1 C
  C19 0.5163(13) 0.4055(17) 0.1121(9) 0.032(3) Uani d P 0.35 . 1 C
  H19A 0.591 0.4569 0.1404 0.038 Uiso d PR 0.35 . 1 H
  H19B 0.4661 0.4865 0.072 0.038 Uiso d PR 0.35 . 1 H
  C20 0.5143(5) 0.2207(9) 0.0842(3) 0.0332(13) Uani d P 0.35 . 1 C
  H20A 0.4439 0.1607 0.0644 0.04 Uiso d PR 0.35 . 1 H
  H20B 0.5737 0.1478 0.1243 0.04 Uiso d PR 0.35 . 1 H
  C21 0.5296(6) 0.2265(9) 0.0288(3) 0.0414(15) Uani d P 0.35 . 1 C
  H21A 0.6017 0.2802 0.0489 0.05 Uiso d PR 0.35 . 1 H
  H21B 0.472 0.3024 -0.0109 0.05 Uiso d PR 0.35 . 1 H
  C22 0.5238(7) 0.0401(11) 0.0012(5) 0.050(2) Uani d P 0.35 . 1 C
  H22A 0.5872 -0.0299 0.0388 0.075 Uiso d PR 0.35 . 1 H
  H22B 0.5243 0.0489 -0.0389 0.075 Uiso d PR 0.35 . 1 H
  H22C 0.4561 -0.0184 -0.0138 0.075 Uiso d PR 0.35 . 1 H
  Cl2 0.52707(18) 0.3704(3) 0.35444(11) 0.0369(5) Uani d P 0.3 . 2 Cl
  N51 0.3803(12) 0.411(2) 0.1564(7) 0.0305(10) Uani d P 0.3 . 2 N
  N61 0.5437(7) 0.3255(11) 0.2513(4) 0.0321(17) Uani d P 0.3 . 2 N
  C151 0.3737(17) 0.432(3) 0.2095(12) 0.0312(13) Uani d P 0.3 . 2 C
  C161 0.280(3) 0.478(5) 0.2044(17) 0.0386(14) Uani d P 0.3 . 2 C
  H16C 0.2173 0.3941 0.1768 0.046 Uiso d PR 0.3 . 2 H
  H16D 0.3019 0.4847 0.2524 0.046 Uiso d PR 0.3 . 2 H
  C171 0.4801(9) 0.3760(15) 0.2696(5) 0.0334(8) Uani d P 0.3 . 2 C
  C181 0.4842(10) 0.3469(13) 0.1833(7) 0.027(2) Uani d P 0.3 . 2 C
  C191 0.5224(8) 0.3115(16) 0.1412(6) 0.033(2) Uani d P 0.3 . 2 C
  H19C 0.4608 0.2611 0.095 0.04 Uiso calc PR 0.3 . 2 H
  H19D 0.5816 0.2211 0.1659 0.04 Uiso calc PR 0.3 . 2 H
  C201 0.5655(9) 0.4798(16) 0.1287(6) 0.039(2) Uani d P 0.3 . 2 C
  H20C 0.5044 0.5651 0.099 0.047 Uiso calc PR 0.3 . 2 H
  H20D 0.5941 0.4464 0.1034 0.047 Uiso calc PR 0.3 . 2 H
  C211 0.6589(7) 0.5713(10) 0.2002(4) 0.0437(18) Uani d P 0.3 . 2 C
  H21C 0.6275 0.6265 0.2212 0.052 Uiso calc PR 0.3 . 2 H
  H21D 0.7133 0.4808 0.2336 0.052 Uiso calc PR 0.3 . 2 H
  C221 0.7134(8) 0.7098(13) 0.1880(5) 0.056(2) Uani d P 0.3 . 2 C
  H22D 0.7439 0.6547 0.1669 0.085 Uiso calc PR 0.3 . 2 H
  H22E 0.7726 0.7651 0.233 0.085 Uiso calc PR 0.3 . 2 H
  H22F 0.6597 0.8009 0.1561 0.085 Uiso calc PR 0.3 . 2 H
  C192 0.5000(12) 0.335(2) 0.1069(10) 0.038(4) Uani d P 0.35 . 3 C
  H19E 0.4316 0.29 0.0624 0.046 Uiso d PR 0.35 . 3 H
  H19F 0.5558 0.2389 0.1278 0.046 Uiso d PR 0.35 . 3 H
  C202 0.5419(8) 0.5052(15) 0.0913(6) 0.058(3) Uani d P 0.35 . 3 C
  H20E 0.5929 0.5695 0.1365 0.07 Uiso d PR 0.35 . 3 H
  H20F 0.5843 0.4671 0.0755 0.07 Uiso d PR 0.35 . 3 H
  C212 0.4563(6) 0.6285(11) 0.0401(4) 0.0519(18) Uani d P 0.35 . 3 C
  H21E 0.4117 0.6641 0.0546 0.062 Uiso d PR 0.35 . 3 H
  H21F 0.4072 0.5672 -0.0059 0.062 Uiso d PR 0.35 . 3 H
  C222 0.5023(8) 0.7938(12) 0.0317(5) 0.066(2) Uani d P 0.35 . 3 C
  H22G 0.5542 0.8515 0.0776 0.099 Uiso d PR 0.35 . 3 H
  H22H 0.4425 0.8766 -0.0008 0.099 Uiso d PR 0.35 . 3 H
  H22I 0.5403 0.7606 0.0128 0.099 Uiso d PR 0.35 . 3 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
  K 0.0327(3) 0.0268(3) 0.0327(3) 0.00300(18) 0.0171(2) 0.00025(18)
  Cl1 0.0698(8) 0.0830(9) 0.0322(6) 0.0411(6) 0.0281(5) 0.0135(5)
  O1 0.0268(7) 0.0344(8) 0.0419(8) 0.0012(6) 0.0158(7) -0.0019(7)
  N1 0.0387(10) 0.0330(10) 0.0386(10) 0.0008(8) 0.0212(9) 0.0028(8)
  N2 0.0403(10) 0.0428(11) 0.0372(10) -0.0040(9) 0.0219(9) 0.0034(9)
  N3 0.0400(10) 0.0376(11) 0.0392(10) -0.0076(8) 0.0258(9) -0.0071(8)
  N4 0.0421(10) 0.0306(10) 0.0436(10) 0.0018(8) 0.0296(9) 0.0003(8)
  N5 0.0232(10) 0.0360(16) 0.025(3) 0.0025(10) 0.0115(19) -0.007(2)
  N6 0.0243(18) 0.0334(18) 0.031(2) 0.0015(14) 0.0138(18) -0.0015(15)
  C1 0.0328(10) 0.0277(11) 0.0251(10) 0.0038(8) 0.0140(9) 0.0006(8)
  C2 0.0352(11) 0.0381(12) 0.0250(10) 0.0106(9) 0.0149(9) 0.0033(9)
  C3 0.0400(12) 0.0479(14) 0.0318(11) 0.0063(10) 0.0165(10) -0.0059(10)
  C4 0.0449(14) 0.079(2) 0.0341(12) 0.0046(13) 0.0211(11) -0.0203(13)
  C5 0.0432(14) 0.091(2) 0.0350(13) 0.0018(14) 0.0244(11) -0.0138(13)
  C6 0.0411(12) 0.0632(16) 0.0348(12) 0.0025(12) 0.0237(11) -0.0032(11)
  C7 0.0353(11) 0.0394(12) 0.0275(10) 0.0105(9) 0.0170(9) 0.0041(9)
  C8 0.0326(11) 0.0368(12) 0.0327(11) 0.0077(9) 0.0191(9) 0.0031(9)
  C9 0.0593(15) 0.0397(13) 0.0395(12) 0.0126(11) 0.0306(12) 0.0100(10)
  C10 0.0544(15) 0.0328(13) 0.0540(15) 0.0129(11) 0.0321(13) 0.0089(11)
  C11 0.0322(11) 0.0389(13) 0.0457(13) 0.0074(10) 0.0228(10) -0.0042(10)
  C12 0.0304(11) 0.0440(13) 0.0352(11) 0.0002(9) 0.0209(9) -0.0050(10)
  C13 0.0307(10) 0.0359(12) 0.0335(11) 0.0034(9) 0.0193(9) 0.0017(9)
  C14 0.0386(12) 0.0418(14) 0.0547(15) 0.0082(11) 0.0243(12) -0.0091(11)
  C15 0.028(2) 0.0295(13) 0.038(4) 0.0018(13) 0.0210(14) -0.003(2)
  C16 0.033(3) 0.038(2) 0.045(3) 0.002(2) 0.0249(14) 0.0108(19)
  C17 0.0323(15) 0.0325(17) 0.028(2) 0.0045(13) 0.0151(16) -0.0009(17)
  C18 0.029(2) 0.046(3) 0.031(3) 0.0073(17) 0.017(2) 0.0019(19)
  C19 0.041(7) 0.025(8) 0.048(7) 0.007(6) 0.036(7) 0.012(7)
  C20 0.038(3) 0.030(4) 0.033(3) 0.004(3) 0.023(3) 0.000(3)
  C21 0.041(3) 0.053(4) 0.034(3) 0.006(3) 0.025(3) 0.008(3)
  C22 0.060(6) 0.050(6) 0.046(4) 0.008(4) 0.036(4) -0.003(4)
  Cl2 0.0420(11) 0.0328(10) 0.0241(11) 0.0032(8) 0.0148(9) -0.0029(8)
  N51 0.0232(10) 0.0360(16) 0.025(3) 0.0025(10) 0.0115(19) -0.007(2)
  N61 0.029(4) 0.031(4) 0.031(5) -0.003(3) 0.016(4) -0.006(3)
  C151 0.028(2) 0.0295(13) 0.038(4) 0.0018(13) 0.0210(14) -0.003(2)
  C161 0.033(3) 0.038(2) 0.045(3) 0.002(2) 0.0249(14) 0.0108(19)
  C171 0.0323(15) 0.0325(17) 0.028(2) 0.0045(13) 0.0151(16) -0.0009(17)
  C181 0.028(5) 0.024(5) 0.030(7) 0.006(4) 0.019(6) -0.004(4)
  C191 0.024(5) 0.035(6) 0.037(5) 0.000(4) 0.017(5) -0.008(5)
  C201 0.048(6) 0.033(6) 0.057(7) -0.003(5) 0.043(6) 0.002(5)
  C211 0.054(5) 0.036(4) 0.057(5) 0.007(4) 0.042(4) 0.001(4)
  C221 0.056(5) 0.060(6) 0.079(6) -0.008(4) 0.054(5) -0.018(5)
  C192 0.022(5) 0.045(10) 0.041(6) 0.004(6) 0.016(5) 0.013(10)
  C202 0.053(5) 0.080(7) 0.051(5) 0.007(5) 0.037(5) 0.014(5)
  C212 0.049(4) 0.061(5) 0.048(4) -0.004(4) 0.031(4) -0.002(4)
  C222 0.072(6) 0.061(5) 0.079(6) -0.003(4) 0.053(5) 0.007(5)
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
  K O1 3_565 2.7535(14) y
  K N4 . 2.7824(18) y
  K N2 3_555 2.840(2) y
  K N1 1_565 2.8479(19) y
  K N3 . 3.0726(19) y
  K N3 3_555 3.2384(19) y
  K N2 1_565 3.265(2) y
  K C12 . 3.434(2) y
  K C11 . 3.450(2) ?
  K K 3_565 4.8797(9) ?
  Cl1 C17 . 1.705(4) y
  O1 C16 . 1.411(13) ?
  O1 C161 . 1.52(3) ?
  O1 H1 . 0.84 ?
  N1 C1 . 1.333(3) ?
  N1 N2 . 1.360(3) ?
  N2 N3 . 1.318(3) ?
  N3 N4 . 1.353(2) ?
  N4 C1 . 1.335(3) ?
  N5 C18 . 1.369(7) ?
  N5 C14 . 1.380(5) ?
  N5 C15 . 1.388(5) ?
  N6 C18 . 1.335(5) ?
  N6 C17 . 1.370(5) ?
  C1 C2 . 1.481(3) ?
  C2 C3 . 1.400(3) ?
  C2 C7 . 1.408(3) ?
  C3 C4 . 1.382(3) ?
  C3 H3 . 0.95 ?
  C4 C5 . 1.377(4) ?
  C4 H4 . 0.95 ?
  C5 C6 . 1.390(4) ?
  C5 H5 . 0.95 ?
  C6 C7 . 1.398(3) ?
  C6 H6 . 0.95 ?
  C7 C8 . 1.488(3) ?
  C8 C9 . 1.391(3) ?
  C8 C13 . 1.399(3) ?
  C9 C10 . 1.383(4) ?
  C9 H9 . 0.95 ?
  C10 C11 . 1.381(3) ?
  C10 H10 . 0.95 ?
  C11 C12 . 1.391(3) ?
  C11 C14 . 1.508(3) ?
  C12 C13 . 1.381(3) ?
  C12 H12 . 0.95 ?
  C13 H13 . 0.95 ?
  C14 N51 . 1.715(13) ?
  C14 H14A . 0.99 ?
  C14 H14B . 0.99 ?
  C15 C17 . 1.336(8) ?
  C15 C16 . 1.513(9) ?
  C16 H16A . 0.99 ?
  C16 H16B . 0.99 ?
  C18 C192 . 1.49(2) ?
  C18 C19 . 1.522(15) ?
  C19 C20 . 1.534(14) ?
  C19 H19A . 0.99 ?
  C19 H19B . 0.99 ?
  C20 C21 . 1.506(9) ?
  C20 H20A . 0.99 ?
  C20 H20B . 0.99 ?
  C21 C22 . 1.527(11) ?
  C21 H21A . 0.99 ?
  C21 H21B . 0.99 ?
  C22 H22A . 0.98 ?
  C22 H22B . 0.98 ?
  C22 H22C . 0.98 ?
  Cl2 C171 . 1.704(9) y
  N51 C151 . 1.363(14) ?
  N51 C181 . 1.401(18) ?
  N61 C181 . 1.305(14) ?
  N61 C171 . 1.366(11) ?
  C151 C161 . 1.43(3) ?
  C151 C171 . 1.43(2) ?
  C161 H16C . 0.99 ?
  C161 H16D . 0.99 ?
  C181 C191 . 1.492(13) ?
  C191 C201 . 1.545(15) ?
  C191 H19C . 0.99 ?
  C191 H19D . 0.99 ?
  C201 C211 . 1.566(14) ?
  C201 H20C . 0.99 ?
  C201 H20D . 0.99 ?
  C211 C221 . 1.483(12) ?
  C211 H21C . 0.99 ?
  C211 H21D . 0.99 ?
  C221 H22D . 0.98 ?
  C221 H22E . 0.98 ?
  C221 H22F . 0.98 ?
  C192 C202 . 1.585(17) ?
  C192 H19E . 0.99 ?
  C192 H19F . 0.99 ?
  C202 C212 . 1.454(12) ?
  C202 H20E . 0.99 ?
  C202 H20F . 0.99 ?
  C212 C222 . 1.509(11) ?
  C212 H21E . 0.99 ?
  C212 H21F . 0.99 ?
  C222 H22G . 0.98 ?
  C222 H22H . 0.98 ?
  C222 H22I . 0.98 ?