#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008303.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_2008303
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  413
_journal_page_last  416
_publ_section_title
;
Two absorption furosemide prodrugs
;
loop_
_publ_author_name
  'Alvaro W. Mombr\'u'
  'Ra\'ul A. Mariezcurrena'
  'Leopoldo Suescun'
  'Helena Pardo'
  'Eduardo Manta'
  'Carolina Prandi'
_chemical_formula_moiety  'C19 H23 Cl N2 O7 S'
_chemical_formula_sum  'C19 H23 Cl N2 O7 S'
_chemical_formula_weight  458.90
_chemical_melting_point  '404-405 K'
_symmetry_cell_setting  Trigonal
_symmetry_space_group_name_H-M  'R -3'
_symmetry_space_group_name_Hall  '-R 3'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-y, x-y, z'
  '-x+y, -x, z'
  'x+2/3, y+1/3, z+1/3'
  '-y+2/3, x-y+1/3, z+1/3'
  '-x+y+2/3, -x+1/3, z+1/3'
  'x+1/3, y+2/3, z+2/3'
  '-y+1/3, x-y+2/3, z+2/3'
  '-x+y+1/3, -x+2/3, z+2/3'
  '-x, -y, -z'
  'y, -x+y, -z'
  'x-y, x, -z'
  '-x+2/3, -y+1/3, -z+1/3'
  'y+2/3, -x+y+1/3, -z+1/3'
  'x-y+2/3, x+1/3, -z+1/3'
  '-x+1/3, -y+2/3, -z+2/3'
  'y+1/3, -x+y+2/3, -z+2/3'
  'x-y+1/3, x+2/3, -z+2/3'
_cell_length_a  36.925(4)
_cell_length_b  36.925(4)
_cell_length_c  8.256(2)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  120.00
_cell_volume  9749(3)
_cell_formula_units_Z  18
_cell_measurement_temperature  273(2)
_exptl_crystal_density_diffrn  1.407
_diffrn_ambient_temperature  273(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
  C1 0.53511(10) 0.05496(10) 0.4722(3) 0.0395(6) Uani d . 1 . . C
  C2 0.55069(10) 0.05926(10) 0.6334(4) 0.0427(7) Uani d . 1 . . C
  C3 0.58268(11) 0.04948(11) 0.6598(4) 0.0454(7) Uani d . 1 . . C
  H3 0.5930(11) 0.0518(11) 0.760(5) 0.050 Uiso d . 1 . . H
  C4 0.59801(10) 0.03651(10) 0.5367(4) 0.0403(7) Uani d . 1 . . C
  C5 0.58136(10) 0.03017(10) 0.3793(3) 0.0388(6) Uani d . 1 . . C
  C6 0.55024(10) 0.03968(10) 0.3517(4) 0.0390(6) Uani d . 1 . . C
  H6 0.5383(10) 0.0369(10) 0.243(4) 0.043 Uiso d . 1 . . H
  C7 0.50244(10) 0.06545(10) 0.4349(4) 0.0438(7) Uani d . 1 . . C
  O1 0.48716(8) 0.07870(9) 0.5317(3) 0.0612(7) Uani d . 1 . . O
  O2 0.49036(7) 0.05883(8) 0.2782(3) 0.0478(6) Uani d . 1 . . O
  N1 0.53561(11) 0.07181(11) 0.7570(3) 0.0553(8) Uani d . 1 . . N
  H1 0.5184(14) 0.0793(14) 0.740(5) 0.066 Uiso d . 1 . . H
  C8 0.54575(15) 0.07022(16) 0.9271(4) 0.0637(11) Uani d D 1 . . C
  H8A 0.5222(10) 0.0668(13) 1.006(5) 0.076 Uiso d D 1 . . H
  H8B 0.5507(14) 0.0449(10) 0.943(5) 0.076 Uiso d D 1 . . H
  C9 0.58411(16) 0.10763(16) 0.9846(5) 0.0727(12) Uani d . 1 . . C
  C10 0.62172(19) 0.1147(2) 1.0277(6) 0.0914(16) Uani d . 1 . . C
  H10 0.6309 0.0954 1.0259 0.101 Uiso calc R 1 . . H
  C11 0.6452(3) 0.1571(3) 1.0770(9) 0.137(3) Uani d . 1 . . C
  H11 0.6720 0.1702 1.1207 0.150 Uiso calc R 1 . . H
  C12 0.6232(3) 0.1741(3) 1.0509(13) 0.164(4) Uani d . 1 . . C
  H12 0.6322 0.2023 1.0682 0.181 Uiso calc R 1 . . H
  O5 0.58405(18) 0.14506(17) 0.9930(7) 0.147(2) Uani d . 1 . . O
  C13 0.45684(12) 0.06591(13) 0.2356(4) 0.0534(8) Uani d D 1 . . C
  H13A 0.4440(12) 0.0466(11) 0.135(4) 0.064 Uiso d D 1 . . H
  H13B 0.4370(11) 0.0584(13) 0.335(4) 0.064 Uiso d D 1 . . H
  O3 0.47266(10) 0.10902(9) 0.2106(3) 0.0686(8) Uani d . 1 . . O
  O4 0.47789(12) 0.10147(14) -0.0571(4) 0.0923(10) Uani d . 1 . . O
  C14 0.48219(17) 0.12318(14) 0.0564(7) 0.0871(14) Uani d DU 1 . . C
  C15 0.4970(2) 0.16799(16) 0.0324(8) 0.138(2) Uani d DU 1 . . C
  H15A 0.4792 0.1707 -0.0465 0.166 Uiso d P 0.50 . . H
  H15B 0.5249 0.1813 -0.0093 0.166 Uiso d P 0.50 . . H
  H15C 0.4738 0.1725 0.0454 0.166 Uiso d P 0.50 . . H
  H15D 0.5074 0.1753 -0.0765 0.166 Uiso d P 0.50 . . H
  C16 0.4975(6) 0.1929(3) 0.1770(13) 0.158(3) Uani d PDU 0.50 . . C
  H16A 0.5168 0.1929 0.2565 0.190 Uiso calc PR 0.50 . . H
  H16B 0.4698 0.1792 0.2255 0.190 Uiso calc PR 0.50 . . H
  C17 0.5100(5) 0.2383(3) 0.137(2) 0.174(4) Uani d PDU 0.50 . . C
  H17A 0.4858 0.2388 0.0947 0.209 Uiso calc PR 0.50 . . H
  H17B 0.5182 0.2544 0.2367 0.209 Uiso calc PR 0.50 . . H
  C18 0.5456(5) 0.2593(5) 0.0158(18) 0.184(4) Uani d PDU 0.50 . . C
  H18A 0.5494 0.2866 -0.0112 0.220 Uiso calc PR 0.50 . . H
  H18B 0.5378 0.2428 -0.0827 0.220 Uiso calc PR 0.50 . . H
  C19 0.5868(5) 0.2647(7) 0.077(3) 0.204(5) Uani d PDU 0.50 . . C
  H19A 0.6080 0.2784 -0.0039 0.245 Uiso calc PR 0.50 . . H
  H19B 0.5836 0.2377 0.1006 0.245 Uiso calc PR 0.50 . . H
  H19C 0.5949 0.2813 0.1742 0.245 Uiso calc PR 0.50 . . H
  C16' 0.5324(5) 0.1991(3) 0.137(2) 0.156(3) Uani d PDU 0.50 . . C
  H16C 0.5585 0.2018 0.0987 0.187 Uiso calc PR 0.50 . . H
  H16D 0.5281 0.1886 0.2474 0.187 Uiso calc PR 0.50 . . H
  C17' 0.5362(4) 0.2423(3) 0.138(2) 0.173(3) Uani d PDU 0.50 . . C
  H17C 0.5297 0.2481 0.0302 0.208 Uiso calc PR 0.50 . . H
  H17D 0.5157 0.2420 0.2120 0.208 Uiso calc PR 0.50 . . H
  C18' 0.5794(5) 0.2772(4) 0.1865(18) 0.196(4) Uani d PDU 0.50 . . C
  H18C 0.5963 0.2652 0.2205 0.235 Uiso calc PR 0.50 . . H
  H18D 0.5769 0.2923 0.2778 0.235 Uiso calc PR 0.50 . . H
  C19' 0.6012(6) 0.3076(6) 0.047(2) 0.223(6) Uani d PDU 0.50 . . C
  H19D 0.6285 0.3289 0.0807 0.267 Uiso calc PR 0.50 . . H
  H19E 0.5851 0.3203 0.0156 0.267 Uiso calc PR 0.50 . . H
  H19F 0.6037 0.2927 -0.0437 0.267 Uiso calc PR 0.50 . . H
  Cl 0.63884(3) 0.02776(3) 0.58242(11) 0.0549(3) Uani d . 1 . . Cl
  S 0.59931(3) 0.01190(3) 0.21737(9) 0.0453(2) Uani d . 1 . . S
  O6 0.64296(8) 0.04106(9) 0.1964(3) 0.0630(7) Uani d . 1 . . O
  O7 0.57131(9) 0.00456(9) 0.0853(3) 0.0594(7) Uani d . 1 . . O
  N2 0.59480(11) -0.03222(11) 0.2637(4) 0.0556(8) Uani d D 1 . . N
  H2A 0.6097(12) -0.0321(13) 0.340(4) 0.067 Uiso d D 1 . . H
  H2B 0.5698(9) -0.0509(12) 0.259(5) 0.067 Uiso d D 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
  C1 0.0419(16) 0.0457(16) 0.0335(14) 0.0240(14) 0.0038(12) 0.0046(12)
  C2 0.0488(17) 0.0466(17) 0.0341(14) 0.0251(14) 0.0036(13) 0.0028(12)
  C3 0.0547(19) 0.0543(19) 0.0338(15) 0.0323(16) -0.0028(13) -0.0003(13)
  C4 0.0422(16) 0.0426(16) 0.0362(15) 0.0214(14) -0.0029(12) 0.0028(12)
  C5 0.0435(16) 0.0436(16) 0.0324(14) 0.0240(14) 0.0038(12) 0.0018(11)
  C6 0.0418(16) 0.0442(16) 0.0313(14) 0.0217(13) 0.0035(12) 0.0037(12)
  C7 0.0469(17) 0.0510(18) 0.0377(15) 0.0275(15) 0.0032(13) 0.0031(13)
  O1 0.0725(17) 0.095(2) 0.0424(12) 0.0619(17) 0.0016(12) -0.0048(13)
  O2 0.0511(13) 0.0675(15) 0.0359(11) 0.0380(12) -0.0019(9) -0.0010(10)
  N1 0.073(2) 0.083(2) 0.0310(13) 0.0545(19) 0.0004(13) -0.0030(13)
  C8 0.084(3) 0.100(3) 0.0291(16) 0.063(3) 0.0042(17) 0.0021(18)
  C9 0.102(4) 0.102(3) 0.041(2) 0.071(3) -0.008(2) -0.012(2)
  C10 0.106(4) 0.123(5) 0.072(3) 0.078(4) 0.004(3) 0.017(3)
  C11 0.124(6) 0.160(8) 0.115(5) 0.062(6) -0.055(5) -0.028(5)
  C12 0.151(8) 0.131(7) 0.208(10) 0.068(6) -0.072(7) -0.100(7)
  O5 0.154(5) 0.140(4) 0.190(5) 0.107(4) -0.058(4) -0.071(4)
  C13 0.0510(19) 0.068(2) 0.0507(19) 0.0373(19) -0.0066(15) 0.0003(17)
  O3 0.084(2) 0.0728(19) 0.0631(17) 0.0503(16) -0.0214(15) -0.0093(14)
  O4 0.103(3) 0.110(3) 0.068(2) 0.057(2) 0.0006(19) 0.013(2)
  C14 0.092(3) 0.080(3) 0.095(3) 0.047(3) -0.034(3) 0.009(3)
  C15 0.154(4) 0.104(3) 0.144(4) 0.054(3) -0.042(4) 0.012(3)
  C16 0.174(5) 0.118(4) 0.167(5) 0.061(4) -0.028(5) 0.005(4)
  C17 0.187(6) 0.129(5) 0.181(6) 0.060(5) -0.021(6) 0.002(5)
  C18 0.195(6) 0.135(5) 0.189(6) 0.058(5) -0.016(6) 0.000(5)
  C19 0.216(8) 0.150(7) 0.201(8) 0.058(7) -0.015(7) 0.001(7)
  C16' 0.172(5) 0.115(4) 0.166(5) 0.060(4) -0.027(5) 0.003(4)
  C17' 0.188(6) 0.128(4) 0.180(5) 0.061(5) -0.019(5) 0.001(4)
  C18' 0.208(7) 0.144(6) 0.195(7) 0.059(6) -0.010(7) -0.003(6)
  C19' 0.228(9) 0.159(8) 0.219(9) 0.050(9) -0.008(9) 0.011(9)
  Cl 0.0563(5) 0.0692(6) 0.0523(5) 0.0413(5) -0.0106(4) -0.0049(4)
  S 0.0507(5) 0.0628(5) 0.0334(4) 0.0366(4) 0.0043(3) 0.0009(3)
  O6 0.0525(15) 0.0854(19) 0.0550(15) 0.0375(14) 0.0172(12) 0.0098(13)
  O7 0.0774(18) 0.0884(19) 0.0369(12) 0.0598(16) -0.0075(11) -0.0090(12)
  N2 0.065(2) 0.066(2) 0.0521(18) 0.0446(17) -0.0053(16) -0.0072(15)
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
  C1 C6 . 1.391(4) ?
  C1 C2 . 1.427(4) ?
  C1 C7 . 1.472(4) ?
  C2 N1 . 1.350(4) ?
  C2 C3 . 1.414(5) ?
  C3 C4 . 1.361(4) ?
  C3 H3 . 0.90(4) ?
  C4 C5 . 1.406(4) ?
  C4 Cl . 1.734(3) ?
  C5 C6 . 1.378(4) ?
  C5 S . 1.769(3) ?
  C6 H6 . 0.98(3) ?
  C7 O1 . 1.213(4) ?
  C7 O2 . 1.350(4) ?
  O2 C13 . 1.431(4) ?
  N1 C8 . 1.462(4) y
  N1 H1 . 0.82(4) ?
  C8 C9 . 1.477(7) y
  C8 H8A . 1.04(2) ?
  C8 H8B . 1.04(2) ?
  C9 C10 . 1.327(7) ?
  C9 O5 . 1.385(6) ?
  C10 C11 . 1.420(10) ?
  C10 H10 . 0.9300 ?
  C11 C12 . 1.269(11) ?
  C11 H11 . 0.9300 ?
  C12 O5 . 1.386(9) ?
  C12 H12 . 0.9300 ?
  C13 O3 . 1.410(5) ?
  C13 H13A . 1.04(2) ?
  C13 H13B . 1.04(2) ?
  O3 C14 . 1.354(6) ?
  O4 C14 . 1.191(6) ?
  C14 C15 . 1.473(4) y
  C15 C16 . 1.501(5) y
  C15 C16' . 1.510(4) y
  C15 H15A . 0.966(6) ?
  C15 H15B . 0.956(9) ?
  C15 H15C . 0.957(8) ?
  C15 H15D . 0.962(8) ?
  C16 C17 . 1.535(5) y
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  C17 C18 . 1.520(5) y
  C17 H17A . 0.9700 ?
  C17 H17B . 0.9700 ?
  C18 C19 . 1.522(5) y
  C18 H18A . 0.9700 ?
  C18 H18B . 0.9700 ?
  C19 H19A . 0.9600 ?
  C19 H19B . 0.9600 ?
  C19 H19C . 0.9600 ?
  C16' C17' . 1.529(5) y
  C16' H16C . 0.9700 ?
  C16' H16D . 0.9700 ?
  C17' C18' . 1.522(5) y
  C17' H17C . 0.9700 ?
  C17' H17D . 0.9700 ?
  C18' C19' . 1.528(5) y
  C18' H18C . 0.9700 ?
  C18' H18D . 0.9700 ?
  C19' H19D . 0.9600 ?
  C19' H19E . 0.9600 ?
  C19' H19F . 0.9600 ?
  S O7 . 1.432(2) ?
  S O6 . 1.432(3) ?
  S N2 . 1.599(3) ?
  N2 H2A . 0.83(3) ?
  N2 H2B . 0.83(3) ?