#------------------------------------------------------------------------------
#$Date: 2020-08-31 15:55:33 +0300 (Mon, 31 Aug 2020) $
#$Revision: 255755 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/83/2008304.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_2008304
loop_
_publ_author_name
'Alvaro W. Mombrú'
'Raúl A. Mariezcurrena'
'Leopoldo Suescun'
'Helena Pardo'
'Eduardo Manta'
'Carolina Prandi'
_publ_section_title
;
 Two absorption furosemide prodrugs
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              413
_journal_page_last               416
_journal_paper_doi               10.1107/S010827019801213X
_journal_volume                  55
_journal_year                    1999
_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          452.5(5)
_chemical_name_systematic
;
benzoyloxymethyl 4-chloro-N-furfuryl-5-sulfamoylanthranilate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.026(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.836(2)
_cell_length_b                   17.605(10)
_cell_length_c                   15.4951(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.31
_cell_measurement_theta_min      18.79
_cell_volume                     2132.3(14)
_computing_cell_refinement       'MSC/AFC Diffractometer Software'
_computing_data_collection
'MSC/AFC Diffractometer Software (Molecular Structure Corporation, 1993)'
_computing_data_reduction        'MSC/AFC Diffractometer Software'
_computing_molecular_graphics    'ZORTEP (Zsolnai & Pritzkow, 1995)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  '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     0.71070
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6393
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  0.8820
_exptl_absorpt_correction_T_min  0.7826
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
'MSC/AFC Diffractometer Software (Molecular Structure Corporation, 1993)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rhombohedral
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.603
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4886
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1355P)²+0.4781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2155
_reflns_number_gt                3298
_reflns_number_total             4886
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sx1070.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 '452-453 K' was changed to '452.5(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 '452-453 K' was changed to '452.5(5)'
- the average value was taken and precision was estimated.

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^)+(0.1355P)^2^+0.4781P] 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^)+(0.1355P)^2^+0.4781P] 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        2132.4(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2008304
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'
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_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'
O O 0.0106 0.0060 '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'
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 119.5(3) ?
C6 C1 C7 120.0(3) ?
C2 C1 C7 120.6(3) ?
N1 C2 C3 120.6(3) ?
N1 C2 C1 121.8(3) ?
C3 C2 C1 117.6(3) ?
C4 C3 C2 120.7(3) ?
C4 C3 H3 116(2) ?
C2 C3 H3 123(2) ?
C3 C4 C5 122.4(3) ?
C3 C4 Cl 116.8(3) ?
C5 C4 Cl 120.8(2) ?
C6 C5 C4 117.5(3) ?
C6 C5 S 118.0(2) ?
C4 C5 S 124.4(2) ?
C5 C6 C1 122.3(3) ?
C5 C6 H6 120(2) ?
C1 C6 H6 118(2) ?
O1 C7 O2 121.7(3) ?
O1 C7 C1 125.6(3) ?
O2 C7 C1 112.8(3) ?
C7 O2 C13 115.2(3) ?
C2 N1 C8 125.2(3) y
C2 N1 H1 113(3) ?
C8 N1 H1 121(3) ?
N1 C8 C9 114.2(3) y
N1 C8 H8A 113(3) ?
C9 C8 H8A 106(3) ?
N1 C8 H8B 104(3) ?
C9 C8 H8B 117(3) ?
H8A C8 H8B 103(4) ?
O5 C9 C10 109.3(6) ?
O5 C9 C8 117.3(5) y
C10 C9 C8 132.9(5) ?
C9 C10 C11 108.1(7) ?
C9 C10 H10 126.0 ?
C11 C10 H10 126.0 ?
C12 C11 C10 105.7(8) ?
C12 C11 H11 127.1 ?
C10 C11 H11 127.1 ?
C11 C12 O5 111.7(8) ?
C11 C12 H12 124.1 ?
O5 C12 H12 124.1 ?
C9 O5 C12 104.8(6) ?
O3 C13 O2 110.0(3) ?
O3 C13 H13A 111(3) ?
O2 C13 H13A 103(3) ?
O3 C13 H13B 109(3) ?
O2 C13 H13B 109(3) ?
H13A C13 H13B 115(4) ?
C14 O3 C13 117.8(3) ?
O4 C14 O3 122.6(3) ?
O4 C14 C15 125.9(4) ?
O3 C14 C15 111.5(3) y
C16 C15 C20 119.9(5) ?
C16 C15 C14 118.9(4) y
C20 C15 C14 121.2(4) y
C15 C16 C17 120.7(6) y
C15 C16 H16 123(4) ?
C17 C16 H16 115(4) ?
C18 C17 C16 118.0(6) y
C18 C17 H17 121.0 ?
C16 C17 H17 121.0 ?
C19 C18 C17 121.6(6) y
C19 C18 H18 119.2 ?
C17 C18 H18 119.2 ?
C18 C19 C20 120.5(6) y
C18 C19 H19 119.8 ?
C20 C19 H19 119.8 ?
C19 C20 C15 119.3(6) y
C19 C20 H20 120(3) ?
C15 C20 H20 121(3) ?
O7 S O6 118.83(18) ?
O7 S N2 107.61(17) ?
O6 S N2 106.55(16) ?
O7 S C5 105.89(15) ?
O6 S C5 107.99(16) ?
N2 S C5 109.81(16) ?
S N2 H2A 112(3) ?
S N2 H2B 114(3) ?
H2A N2 H2B 128(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 . 1.401(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) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . 0.82(3) 2.01(4) 2.689(4) 140(4) y
N1 H1 O4 1_455 0.82(3) 2.49(4) 3.079(5) 129(3) y
N2 H2A O1 4_666 0.83(3) 2.30(4) 3.004(4) 143(4) y
N2 H2A O4 4_566 0.83(3) 2.51(4) 3.105(5) 129(4) y
N2 H2B O6 3_567 0.83(4) 2.20(4) 3.006(4) 162(4) y
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 -178.4(3) ?
C7 C1 C2 N1 1.0(5) ?
C6 C1 C2 C3 -0.4(4) ?
C7 C1 C2 C3 179.1(3) ?
N1 C2 C3 C4 178.4(3) ?
C1 C2 C3 C4 0.3(5) ?
C2 C3 C4 C5 0.9(5) ?
C2 C3 C4 Cl -177.7(3) ?
C3 C4 C5 C6 -2.0(5) ?
Cl C4 C5 C6 176.5(2) ?
C3 C4 C5 S 174.2(3) ?
Cl C4 C5 S -7.3(4) ?
C4 C5 C6 C1 1.9(5) ?
S C5 C6 C1 -174.5(2) ?
C2 C1 C6 C5 -0.8(5) ?
C7 C1 C6 C5 179.7(3) ?
C6 C1 C7 O1 -178.7(3) ?
C2 C1 C7 O1 1.8(5) ?
C6 C1 C7 O2 1.5(4) ?
C2 C1 C7 O2 -178.0(3) ?
O1 C7 O2 C13 -4.3(5) ?
C1 C7 O2 C13 175.5(3) ?
C3 C2 N1 C8 7.5(5) ?
C1 C2 N1 C8 -174.5(3) y
C2 N1 C8 C9 84.6(5) y
N1 C8 C9 O5 57.7(7) y
N1 C8 C9 C10 -113.6(7) ?
O5 C9 C10 C11 4.7(9) ?
C8 C9 C10 C11 176.5(7) ?
C9 C10 C11 C12 -1.6(12) ?
C10 C11 C12 O5 -1.9(13) ?
C10 C9 O5 C12 -5.6(9) ?
C8 C9 O5 C12 -178.8(7) ?
C11 C12 O5 C9 4.8(12) ?
C7 O2 C13 O3 80.6(4) ?
O2 C13 O3 C14 85.3(4) ?
C13 O3 C14 O4 1.4(5) ?
C13 O3 C14 C15 -177.8(3) y
O4 C14 C15 C16 -11.4(6) ?
O3 C14 C15 C16 167.8(4) y
O4 C14 C15 C20 170.0(4) ?
O3 C14 C15 C20 -10.7(5) y
C20 C15 C16 C17 1.5(7) ?
C14 C15 C16 C17 -177.0(4) y
C15 C16 C17 C18 -0.4(9) ?
C16 C17 C18 C19 -1.2(10) y
C17 C18 C19 C20 1.6(10) ?
C18 C19 C20 C15 -0.4(8) y
C16 C15 C20 C19 -1.2(7) ?
C14 C15 C20 C19 177.3(4) ?
C6 C5 S O7 -8.8(3) ?
C4 C5 S O7 175.1(3) ?
C6 C5 S O6 119.5(3) ?
C4 C5 S O6 -56.6(3) ?
C6 C5 S N2 -124.7(3) ?
C4 C5 S N2 59.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21136512
