#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008304.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_2008304
_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  'C20 H17 Cl N2 O7 S'
_chemical_formula_sum  'C20 H17 Cl N2 O7 S'
_chemical_formula_weight  464.87
_chemical_melting_point  '452-453 K'
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  7.836(2)
_cell_length_b  17.605(10)
_cell_length_c  15.4951(18)
_cell_angle_alpha  90.00
_cell_angle_beta  94.026(16)
_cell_angle_gamma  90.00
_cell_volume  2132.4(13)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.448
_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
  C1 -0.2634(4) 0.32661(18) 0.69390(18) 0.0428(6) Uani d . 1 . . C
  C2 -0.4254(4) 0.36074(18) 0.7051(2) 0.0451(7) Uani d . 1 . . C
  C3 -0.4392(4) 0.4079(2) 0.7787(2) 0.0479(7) Uani d D 1 . . C
  H3 -0.546(4) 0.429(2) 0.794(2) 0.058 Uiso d D 1 . . H
  C4 -0.3013(4) 0.42005(18) 0.8359(2) 0.0457(7) Uani d . 1 . . C
  C5 -0.1405(4) 0.38812(18) 0.82496(18) 0.0415(6) Uani d . 1 . . C
  C6 -0.1259(4) 0.34094(18) 0.75446(19) 0.0429(6) Uani d D 1 . . C
  H6 -0.020(4) 0.3164(19) 0.746(2) 0.051 Uiso d D 1 . . H
  C7 -0.2404(4) 0.27627(19) 0.6201(2) 0.0458(7) Uani d . 1 . . C
  O1 -0.3480(3) 0.26110(16) 0.56386(16) 0.0592(7) Uani d . 1 . . O
  O2 -0.0788(3) 0.24657(14) 0.62093(14) 0.0515(6) Uani d . 1 . . O
  N1 -0.5627(4) 0.34741(19) 0.6499(2) 0.0544(7) Uani d D 1 . . N
  H1 -0.543(5) 0.319(2) 0.610(2) 0.056(11) Uiso d D 1 . . H
  C8 -0.7282(5) 0.3848(3) 0.6523(3) 0.0615(9) Uani d DU 1 . . C
  H8A -0.756(6) 0.394(3) 0.706(2) 0.074 Uiso d D 1 . . H
  H8B -0.804(5) 0.349(2) 0.634(3) 0.074 Uiso d D 1 . . H
  C9 -0.7395(7) 0.4584(3) 0.6073(3) 0.0844(12) Uani d U 1 . . C
  C10 -0.7569(11) 0.5285(4) 0.6343(5) 0.1234(18) Uani d DU 1 . . C
  H10 -0.7724(12) 0.5442(7) 0.6940(19) 0.148 Uiso calc RD 1 . . H
  C11 -0.7497(13) 0.5771(5) 0.5628(6) 0.144(2) Uani d DU 1 . . C
  H11 -0.7616(13) 0.6323(18) 0.5622(6) 0.173 Uiso calc RD 1 . . H
  C12 -0.7255(14) 0.5359(5) 0.5013(6) 0.155(2) Uani d DU 1 . . C
  H12 -0.7182(14) 0.5541(8) 0.442(2) 0.186 Uiso calc RD 1 . . H
  O5 -0.7093(8) 0.4591(3) 0.5263(3) 0.1442(16) Uani d U 1 . . O
  C13 -0.0530(5) 0.1930(2) 0.5544(2) 0.0564(8) Uani d D 1 . . C
  H13A 0.041(4) 0.167(2) 0.575(3) 0.068 Uiso d D 1 . . H
  H13B -0.146(4) 0.165(2) 0.546(3) 0.068 Uiso d D 1 . . H
  O3 -0.0256(3) 0.23095(16) 0.47683(15) 0.0568(6) Uani d . 1 . . O
  C14 0.1352(5) 0.2536(2) 0.4640(2) 0.0528(8) Uani d . 1 . . C
  O4 0.2541(3) 0.24134(19) 0.51524(18) 0.0692(8) Uani d . 1 . . O
  C15 0.1423(6) 0.2951(2) 0.3815(2) 0.0648(10) Uani d . 1 . . C
  C16 0.2869(8) 0.3340(3) 0.3662(3) 0.0861(14) Uani d D 1 . . C
  H16 0.396(5) 0.325(3) 0.398(3) 0.103 Uiso d D 1 . . H
  C17 0.2961(12) 0.3774(4) 0.2897(5) 0.117(2) Uani d D 1 . . C
  H17 0.397(3) 0.4052(9) 0.2788(6) 0.140 Uiso calc RD 1 . . H
  C18 0.1535(13) 0.3785(4) 0.2311(4) 0.112(2) Uani d D 1 . . C
  H18 0.1564(13) 0.4086(10) 0.1791(17) 0.135 Uiso calc RD 1 . . H
  C19 0.0114(10) 0.3386(4) 0.2450(4) 0.104(2) Uani d D 1 . . C
  H19 -0.085(3) 0.3395(4) 0.2022(13) 0.125 Uiso calc RD 1 . . H
  C20 0.0019(7) 0.2963(3) 0.3202(3) 0.0780(13) Uani d D 1 . . C
  H20 -0.102(5) 0.268(3) 0.330(4) 0.094 Uiso d D 1 . . H
  Cl -0.33490(12) 0.47592(6) 0.92566(6) 0.0613(3) Uani d . 1 . . Cl
  S 0.04701(10) 0.40838(5) 0.89142(5) 0.0462(3) Uani d . 1 . . S
  O6 0.0746(3) 0.48885(15) 0.88979(16) 0.0596(7) Uani d . 1 . . O
  O7 0.1760(3) 0.35934(17) 0.86259(16) 0.0650(7) Uani d . 1 . . O
  N2 0.0185(4) 0.38665(18) 0.98936(18) 0.0544(7) Uani d D 1 . . N
  H2A 0.013(6) 0.3400(17) 0.997(3) 0.065 Uiso d D 1 . . H
  H2B -0.028(5) 0.421(2) 1.016(3) 0.065 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 0.0440(15) 0.0471(16) 0.0374(14) -0.0052(13) 0.0041(11) -0.0043(12)
  C2 0.0425(15) 0.0509(17) 0.0416(15) -0.0061(13) 0.0012(12) -0.0035(12)
  C3 0.0424(16) 0.0545(19) 0.0470(16) -0.0007(14) 0.0030(13) -0.0065(13)
  C4 0.0483(16) 0.0493(17) 0.0392(14) -0.0045(13) 0.0020(12) -0.0071(12)
  C5 0.0414(14) 0.0473(16) 0.0353(13) -0.0032(12) -0.0021(11) -0.0028(12)
  C6 0.0418(15) 0.0492(17) 0.0375(14) -0.0014(13) 0.0014(11) -0.0026(12)
  C7 0.0429(15) 0.0506(17) 0.0440(15) -0.0062(13) 0.0038(12) -0.0043(13)
  O1 0.0531(14) 0.0721(16) 0.0514(13) -0.0029(12) -0.0032(11) -0.0216(12)
  O2 0.0483(12) 0.0612(14) 0.0453(12) -0.0013(10) 0.0049(10) -0.0128(10)
  N1 0.0459(15) 0.0666(19) 0.0497(15) -0.0005(13) -0.0027(12) -0.0139(14)
  C8 0.0452(17) 0.085(3) 0.0546(19) -0.0016(17) 0.0038(15) -0.0140(18)
  C9 0.080(2) 0.099(3) 0.076(2) 0.035(2) 0.021(2) 0.001(2)
  C10 0.153(4) 0.107(3) 0.112(3) 0.039(3) 0.022(3) 0.005(3)
  C11 0.183(5) 0.118(4) 0.135(4) 0.052(4) 0.036(4) 0.024(3)
  C12 0.207(5) 0.137(4) 0.126(4) 0.050(4) 0.044(4) 0.038(3)
  O5 0.199(4) 0.137(3) 0.101(3) 0.058(3) 0.044(3) 0.023(2)
  C13 0.0529(19) 0.060(2) 0.0561(19) -0.0035(16) 0.0051(16) -0.0159(16)
  O3 0.0487(13) 0.0778(17) 0.0438(12) 0.0007(12) 0.0017(10) -0.0107(11)
  C14 0.0533(18) 0.056(2) 0.0489(18) 0.0019(15) 0.0039(15) -0.0155(14)
  O4 0.0499(14) 0.094(2) 0.0631(16) -0.0032(14) -0.0009(12) -0.0057(14)
  C15 0.080(3) 0.059(2) 0.057(2) 0.0055(19) 0.0149(19) -0.0135(17)
  C16 0.097(4) 0.087(3) 0.077(3) -0.016(3) 0.018(3) -0.006(3)
  C17 0.163(7) 0.089(4) 0.103(5) -0.027(4) 0.049(5) -0.007(3)
  C18 0.172(7) 0.088(4) 0.080(4) 0.023(4) 0.024(4) 0.009(3)
  C19 0.131(5) 0.113(5) 0.068(3) 0.044(4) 0.012(3) 0.012(3)
  C20 0.087(3) 0.090(3) 0.058(2) 0.025(3) 0.005(2) -0.002(2)
  Cl 0.0608(5) 0.0715(6) 0.0514(5) 0.0044(4) 0.0018(4) -0.0227(4)
  S 0.0449(4) 0.0549(5) 0.0377(4) -0.0029(3) -0.0048(3) -0.0030(3)
  O6 0.0667(15) 0.0607(15) 0.0501(13) -0.0173(12) -0.0053(11) -0.0001(11)
  O7 0.0482(14) 0.091(2) 0.0539(14) 0.0081(13) -0.0064(11) -0.0142(13)
  N2 0.0711(19) 0.0516(16) 0.0390(14) 0.0031(15) -0.0059(12) 0.0026(12)
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 . 1.401(4) ?
  C1 C2 . 1.426(5) ?
  C1 C7 . 1.468(4) ?
  C2 N1 . 1.348(4) ?
  C2 C3 . 1.421(4) ?
  C3 C4 . 1.366(5) ?
  C3 H3 . 0.97(3) ?
  C4 C5 . 1.400(4) ?
  C4 Cl . 1.739(3) ?
  C5 C6 . 1.383(4) ?
  C5 S . 1.771(3) ?
  C6 H6 . 0.95(2) ?
  C7 O1 . 1.199(4) ?
  C7 O2 . 1.369(4) ?
  O2 C13 . 1.422(4) ?
  N1 C8 . 1.456(5) y
  N1 H1 . 0.82(3) ?
  C8 C9 . 1.473(7) y
  C8 H8A . 0.89(3) ?
  C8 H8B . 0.90(3) ?
  C9 O5 . 1.293(6) ?
  C9 C10 . 1.313(8) ?
  C10 C11 . 1.404(10) ?
  C10 H10 . 0.9814 ?
  C11 C12 . 1.223(11) ?
  C11 H11 . 0.9765 ?
  C12 O5 . 1.410(9) ?
  C12 H12 . 0.9843 ?
  C13 O3 . 1.406(5) ?
  C13 H13A . 0.90(3) ?
  C13 H13B . 0.89(3) ?
  O3 C14 . 1.350(4) ?
  C14 O4 . 1.201(4) ?
  C14 C15 . 1.477(5) y
  C15 C16 . 1.359(7) y
  C15 C20 . 1.402(7) y
  C16 C17 . 1.416(8) y
  C16 H16 . 0.97(3) ?
  C17 C18 . 1.390(11) y
  C17 H17 . 0.9566 ?
  C18 C19 . 1.347(10) y
  C18 H18 . 0.9648 ?
  C19 C20 . 1.391(7) y
  C19 H19 . 0.9688 ?
  C20 H20 . 0.98(3) ?
  S O7 . 1.425(3) ?
  S O6 . 1.434(3) ?
  S N2 . 1.596(3) ?
  N2 H2A . 0.83(3) ?
  N2 H2B . 0.83(3) ?