#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/80/2008037.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2008037
loop_
_publ_author_name
'Suescun, Leopoldo '
'Mariezcurrena, Raúl A. '
'Mombrú, Alvaro W. '
'González, Oscar A. '
'Manta, Eduardo '
'Prandi, Carolina '
_publ_section_title
;
 Three Isostructural Furosemide Prodrugs
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1911
_journal_page_last               1915
_journal_paper_doi               10.1107/S0108270198007653
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C17 H19 Cl N2 O7 S'
_chemical_formula_weight         430.85
_chemical_melting_point          438.5(5)
_chemical_name_systematic
;
isobutyryloxymethyl 4-chloro-N-furfuryl-5-sulfamoylanthranilate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                107.78(2)
_cell_angle_beta                 107.76(2)
_cell_angle_gamma                102.863(14)
_cell_formula_units_Z            2
_cell_length_a                   10.580(2)
_cell_length_b                   12.471(2)
_cell_length_c                   8.643(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      12.5
_cell_volume                     969.4(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_data_reduction        'MSC/AFC Diffractometer Control Software'
_computing_molecular_graphics    'ZORTEP (Zsolnai & Pritzkow, 1995)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Rigaku AFC7S'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.035
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4701
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(Molecular Structure Corporation, 1993)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             448
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.622
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.089
_refine_ls_goodness_of_fit_obs   1.137
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4458
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.113
_refine_ls_restrained_S_obs      1.164
_refine_ls_R_factor_all          0.069
_refine_ls_R_factor_obs          0.058
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0896P)²+0.8658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.180
_refine_ls_wR_factor_obs         0.169
_reflns_number_observed          3668
_reflns_number_total             4459
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            sx1045.cif
_cod_data_source_block           IV
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '438-439 K' was changed to '438.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '438-439 K' was changed to '438.5(5)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0896P)^2^+0.8658P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0896P)^2^+0.8658P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        969.4(4)
_cod_original_formula_sum        'C17 H19 Cl N2 O7 S1'
_cod_database_code               2008037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.4758(3) 0.3450(2) -0.0094(3) 0.0315(5) Uani d . 1 . C
C2 0.4281(3) 0.3282(2) -0.1908(3) 0.0317(5) Uani d . 1 . C
C3 0.2952(3) 0.3380(2) -0.2686(4) 0.0356(5) Uani d . 1 . C
H3 0.260(4) 0.324(3) -0.382(5) 0.046(9) Uiso d . 1 . H
C4 0.2178(3) 0.3663(2) -0.1705(3) 0.0346(5) Uani d . 1 . C
C5 0.2650(3) 0.3844(2) 0.0087(3) 0.0327(5) Uani d . 1 . C
C6 0.3943(3) 0.3731(2) 0.0862(3) 0.0329(5) Uani d . 1 . C
H6 0.431(4) 0.385(3) 0.204(5) 0.053(10) Uiso d . 1 . H
C7 0.6125(3) 0.3338(2) 0.0795(3) 0.0343(5) Uani d . 1 . C
O1 0.6847(2) 0.2966(2) 0.0078(3) 0.0473(5) Uani d . 1 . O
O2 0.6502(2) 0.3700(2) 0.2567(3) 0.0482(5) Uani d . 1 . O
C13 0.7811(3) 0.3623(3) 0.3543(4) 0.0466(7) Uani d . 1 . C
H13A 0.807(4) 0.416(4) 0.478(6) 0.063(11) Uiso d . 1 . H
H13B 0.852(4) 0.382(3) 0.307(4) 0.041(8) Uiso d . 1 . H
O3 0.7522(2) 0.2464(2) 0.3555(3) 0.0566(6) Uani d . 1 . O
C14 0.8240(4) 0.1776(3) 0.2963(5) 0.0511(7) Uani d . 1 . C
O4 0.9164(3) 0.2114(2) 0.2531(4) 0.0580(6) Uani d . 1 . O
C15 0.7741(7) 0.0572(5) 0.3036(11) 0.110(2) Uani d U 1 . C
H15 0.7795(7) 0.0723(5) 0.4239(11) 0.132 Uiso calc R 1 . H
C16 0.8654(10) -0.0136(7) 0.2723(16) 0.178(4) Uani d U 1 . C
H16A 0.9620(10) 0.0332(7) 0.3530(16) 0.214 Uiso calc R 1 . H
H16B 0.8579(10) -0.0347(7) 0.1525(16) 0.214 Uiso calc R 1 . H
H16C 0.8358(10) -0.0855(7) 0.2910(16) 0.214 Uiso calc R 1 . H
C17 0.6305(10) -0.0110(7) 0.1848(16) 0.193(4) Uani d U 1 . C
H17A 0.5721(10) 0.0359(7) 0.2062(16) 0.232 Uiso calc R 1 . H
H17B 0.6002(10) -0.0828(7) 0.2033(16) 0.232 Uiso calc R 1 . H
H17C 0.6223(10) -0.0320(7) 0.0647(16) 0.232 Uiso calc R 1 . H
N1 0.5062(3) 0.3057(2) -0.2863(3) 0.0415(5) Uani d . 1 . N
H1 0.579(4) 0.304(3) -0.238(5) 0.047(10) Uiso d . 1 . H
C8 0.4662(4) 0.2898(3) -0.4700(4) 0.0471(7) Uani d . 1 . C
H8A 0.554(4) 0.303(4) -0.496(5) 0.063(11) Uiso d . 1 . H
H8B 0.427(4) 0.351(4) -0.501(5) 0.065(11) Uiso d . 1 . H
C9 0.3660(4) 0.1681(3) -0.5979(4) 0.0540(8) Uani d . 1 . C
C10 0.2330(5) 0.1239(4) -0.7154(6) 0.0869(15) Uani d . 1 . C
H10 0.1738(5) 0.1671(4) -0.7396(6) 0.104 Uiso calc R 1 . H
C11 0.1984(8) -0.0030(5) -0.7975(9) 0.121(2) Uani d . 1 . C
H11 0.1125(8) -0.0584(5) -0.8865(9) 0.145 Uiso calc R 1 . H
C12 0.3097(8) -0.0260(5) -0.7241(10) 0.125(3) Uani d . 1 . C
H12 0.3156(8) -0.1024(5) -0.7530(10) 0.149 Uiso calc R 1 . H
O5 0.4172(4) 0.0768(3) -0.5988(5) 0.0949(11) Uani d . 1 . O
Cl 0.05816(8) 0.37953(8) -0.27533(10) 0.0523(2) Uani d . 1 . Cl
S 0.17755(7) 0.43322(6) 0.14680(9) 0.0359(2) Uani d . 1 . S
O6 0.1755(2) 0.5490(2) 0.1516(3) 0.0453(5) Uani d . 1 . O
O7 0.2469(2) 0.4238(2) 0.3099(3) 0.0516(6) Uani d . 1 . O
N2 0.0181(3) 0.3405(3) 0.0545(4) 0.0500(6) Uani d . 1 . N
H2A -0.042(5) 0.365(4) -0.012(6) 0.079(14) Uiso d . 1 . H
H2B -0.001(5) 0.297(4) 0.102(6) 0.064(12) Uiso d . 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 120.2(2) ?
C6 C1 C7 119.4(2) ?
C2 C1 C7 120.4(2) ?
N1 C2 C3 120.4(2) ?
N1 C2 C1 122.2(2) ?
C3 C2 C1 117.4(2) ?
C4 C3 C2 120.9(2) ?
C4 C3 H3 119.(2) ?
C2 C3 H3 120.(2) ?
C3 C4 C5 122.0(2) ?
C3 C4 Cl 117.7(2) ?
C5 C4 Cl 120.4(2) ?
C6 C5 C4 117.9(2) ?
C6 C5 S 117.9(2) ?
C4 C5 S 124.0(2) ?
C5 C6 C1 121.7(2) ?
C5 C6 H6 122.(2) ?
C1 C6 H6 117.(2) ?
O1 C7 O2 122.1(2) ?
O1 C7 C1 125.9(2) ?
O2 C7 C1 112.0(2) ?
C7 O2 C13 116.1(2) ?
O3 C13 O2 107.6(3) ?
O3 C13 H13A 104.(2) ?
O2 C13 H13A 104.(2) ?
O3 C13 H13B 113.8(19) ?
O2 C13 H13B 111.5(19) ?
H13A C13 H13B 115.(3) ?
C14 O3 C13 118.6(2) ?
O4 C14 O3 123.8(3) ?
O4 C14 C15 126.2(4) no
O3 C14 C15 109.9(3) no
C17 C15 C16 110.2(7) no
C17 C15 C14 112.4(6) no
C16 C15 C14 112.5(5) no
C17 C15 H15 107.1(6) ?
C16 C15 H15 107.1(5) ?
C14 C15 H15 107.1(3) ?
C15 C16 H16A 109.5(5) ?
C15 C16 H16B 109.5(5) ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5(4) ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C15 C17 H17A 109.5(5) ?
C15 C17 H17B 109.5(5) ?
H17A C17 H17B 109.5 ?
C15 C17 H17C 109.5(6) ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C2 N1 C8 125.4(3) ?
C2 N1 H1 117.(3) ?
C8 N1 H1 118.(3) ?
N1 C8 C9 113.5(3) ?
N1 C8 H8A 109.(2) ?
C9 C8 H8A 107.(2) ?
N1 C8 H8B 115.(2) ?
C9 C8 H8B 109.(2) ?
H8A C8 H8B 103.(3) ?
C10 C9 O5 109.6(4) ?
C10 C9 C8 135.0(4) ?
O5 C9 C8 115.4(3) ?
C9 C10 C11 106.6(5) ?
C9 C10 H10 126.7(3) ?
C11 C10 H10 126.7(4) ?
C12 C11 C10 106.8(5) ?
C12 C11 H11 126.6(3) ?
C10 C11 H11 126.6(4) ?
C11 C12 O5 111.0(5) ?
C11 C12 H12 124.5(4) ?
O5 C12 H12 124.5(3) ?
C12 O5 C9 106.0(4) ?
O7 S O6 118.57(15) ?
O7 S N2 108.0(2) ?
O6 S N2 108.92(15) ?
O7 S C5 106.52(12) ?
O6 S C5 106.76(13) ?
N2 S C5 107.54(15) ?
S N2 H2A 113.(3) ?
S N2 H2B 116.(3) ?
H2A N2 H2B 127.(4) ?
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 . 1.394(4) ?
C1 C2 . 1.424(4) ?
C1 C7 . 1.475(3) ?
C2 N1 . 1.349(3) ?
C2 C3 . 1.412(4) ?
C3 C4 . 1.372(4) ?
C3 H3 . 0.88(4) ?
C4 C5 . 1.401(4) ?
C4 Cl . 1.727(3) ?
C5 C6 . 1.387(3) ?
C5 S . 1.770(3) ?
C6 H6 . 0.92(4) ?
C7 O1 . 1.206(3) ?
C7 O2 . 1.354(3) ?
O2 C13 . 1.426(3) ?
C13 O3 . 1.413(4) ?
C13 H13A . 0.99(4) ?
C13 H13B . 0.98(3) ?
O3 C14 . 1.355(4) ?
C14 O4 . 1.187(4) ?
C14 C15 . 1.503(5) no
C15 C17 . 1.423(11) no
C15 C16 . 1.477(10) no
C15 H15 . 0.98 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
N1 C8 . 1.449(4) ?
N1 H1 . 0.76(4) ?
C8 C9 . 1.481(5) ?
C8 H8A . 1.01(4) ?
C8 H8B . 1.01(4) ?
C9 C10 . 1.325(6) ?
C9 O5 . 1.365(4) ?
C10 C11 . 1.428(7) ?
C10 H10 . 0.93 ?
C11 C12 . 1.295(9) ?
C11 H11 . 0.93 ?
C12 O5 . 1.364(7) ?
C12 H12 . 0.93 ?
S O7 . 1.431(2) ?
S O6 . 1.436(2) ?
S N2 . 1.602(3) ?
N2 H2A . 0.89(5) ?
N2 H2B . 0.80(4) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 N1 177.2(2) ?
C7 C1 C2 N1 -2.2(4) ?
C6 C1 C2 C3 -1.7(4) ?
C7 C1 C2 C3 178.9(2) ?
N1 C2 C3 C4 -177.0(3) ?
C1 C2 C3 C4 1.9(4) ?
C2 C3 C4 C5 -1.1(4) ?
C2 C3 C4 Cl 178.6(2) ?
C3 C4 C5 C6 0.0(4) ?
Cl C4 C5 C6 -179.7(2) ?
C3 C4 C5 S 174.5(2) ?
Cl C4 C5 S -5.3(3) ?
C4 C5 C6 C1 0.2(4) ?
S C5 C6 C1 -174.6(2) ?
C2 C1 C6 C5 0.7(4) ?
C7 C1 C6 C5 -179.9(2) ?
C6 C1 C7 O1 170.9(3) ?
C2 C1 C7 O1 -9.7(4) ?
C6 C1 C7 O2 -8.7(3) ?
C2 C1 C7 O2 170.8(2) ?
O1 C7 O2 C13 0.3(4) ?
C1 C7 O2 C13 179.9(2) ?
C7 O2 C13 O3 -88.6(3) no
O2 C13 O3 C14 125.2(3) no
C13 O3 C14 O4 4.7(5) no
C13 O3 C14 C15 -178.2(4) ?
O4 C14 C15 C17 -117.6(7) ?
O3 C14 C15 C17 65.4(8) no
O4 C14 C15 C16 7.5(9) ?
O3 C14 C15 C16 -169.5(7) no
C3 C2 N1 C8 0.0(4) ?
C1 C2 N1 C8 -178.8(3) ?
C2 N1 C8 C9 -80.2(4) no
N1 C8 C9 C10 114.7(5) no
N1 C8 C9 O5 -64.6(4) ?
O5 C9 C10 C11 -0.8(6) ?
C8 C9 C10 C11 179.9(5) ?
C9 C10 C11 C12 0.7(8) ?
C10 C11 C12 O5 -0.3(9) ?
C11 C12 O5 C9 -0.2(8) ?
C10 C9 O5 C12 0.6(6) ?
C8 C9 O5 C12 -180.0(4) ?
C6 C5 S O7 -13.7(3) ?
C4 C5 S O7 171.9(2) ?
C6 C5 S O6 113.9(2) ?
C4 C5 S O6 -60.5(3) ?
C6 C5 S N2 -129.3(2) ?
C4 C5 S N2 56.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21136657
