#------------------------------------------------------------------------------
#$Date: 2017-12-01 16:42:51 +0200 (Fri, 01 Dec 2017) $
#$Revision: 203864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/83/1548352.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_1548352
loop_
_publ_author_name
'N. Rajesh Goud'
'Swarupa Gangavaram'
'Kuthuru Suresh'
'Sharmistha Pal'
'Sulur G. Manjunatha'
'Sudhir Nambiar'
'Ashwini Nangia'
_publ_section_title
;
 Novel furosemide cocrystals and selection of high solubility drug forms
;
_journal_name_full               'Journal of Pharmaceutical Sciences'
_journal_page_first              664
_journal_page_last               680
_journal_paper_doi               10.1002/jps.22805
_journal_volume                  101
_journal_year                    2012
_chemical_formula_sum            'C20 H18 Cl N6 O7 S'
_chemical_formula_weight         521.91
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                95.387(5)
_cell_angle_beta                 102.271(5)
_cell_angle_gamma                110.101(5)
_cell_formula_units_Z            2
_cell_length_a                   7.512(2)
_cell_length_b                   9.462(3)
_cell_length_c                   17.198(5)
_cell_measurement_reflns_used    3358
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.33
_cell_volume                     1103.0(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8290
_diffrn_reflns_theta_full        25.90
_diffrn_reflns_theta_max         25.90
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  0.9259
_exptl_absorpt_correction_T_min  0.8593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             538
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0735
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0753P)²+2.8625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1782
_refine_ls_wR_factor_ref         0.1874
_reflns_number_gt                3388
_reflns_number_total             4045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1.cif
_cod_data_source_block           FUROS-CAF
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1548352
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5083(6) 0.3072(5) 0.3651(3) 0.0215(9) Uani 1 1 d . . .
H1A H 0.3869 0.2446 0.3747 0.032 Uiso 1 1 calc R . .
H1B H 0.6089 0.3442 0.4153 0.032 Uiso 1 1 calc R . .
H1C H 0.5455 0.2476 0.3279 0.032 Uiso 1 1 calc R . .
C2 C 0.2190(6) 0.5023(5) 0.1413(2) 0.0225(9) Uani 1 1 d . . .
H2A H 0.2958 0.4978 0.1038 0.034 Uiso 1 1 calc R . .
H2B H 0.1679 0.5814 0.1332 0.034 Uiso 1 1 calc R . .
H2C H 0.1122 0.4057 0.1327 0.034 Uiso 1 1 calc R . .
C3 C 0.3702(6) 0.4115(5) 0.2537(2) 0.0188(8) Uani 1 1 d . . .
C4 C 0.5628(5) 0.5815(4) 0.3753(2) 0.0164(8) Uani 1 1 d . . .
C5 C 0.5318(5) 0.7022(4) 0.3455(2) 0.0170(8) Uani 1 1 d . . .
C6 C 0.4194(6) 0.6872(4) 0.2661(2) 0.0177(8) Uani 1 1 d . . .
C7 C 0.7190(6) 0.7757(5) 0.4683(2) 0.0210(9) Uani 1 1 d . . .
H7 H 0.7976 0.8381 0.5174 0.025 Uiso 1 1 calc R . .
C8 C 0.6403(6) 0.9825(4) 0.4091(3) 0.0222(9) Uani 1 1 d . . .
H8A H 0.7178 1.0439 0.4610 0.033 Uiso 1 1 calc R . .
H8B H 0.5094 0.9819 0.3996 0.033 Uiso 1 1 calc R . .
H8C H 0.6982 1.0246 0.3676 0.033 Uiso 1 1 calc R . .
C9 C 0.9408(6) 0.7135(4) 0.2682(2) 0.0182(8) Uani 1 1 d . . .
C10 C 0.8084(5) 0.6197(4) 0.1955(2) 0.0161(8) Uani 1 1 d . . .
C11 C 0.7527(5) 0.4643(4) 0.1837(2) 0.0167(8) Uani 1 1 d . . .
H11 H 0.6627 0.4053 0.1358 0.020 Uiso 1 1 calc R . .
C12 C 0.8285(5) 0.3919(4) 0.2426(2) 0.0166(8) Uani 1 1 d . A .
C13 C 0.9631(6) 0.4839(4) 0.3149(2) 0.0169(8) Uani 1 1 d . . .
C14 C 1.0131(5) 0.6429(4) 0.3260(2) 0.0145(8) Uani 1 1 d . . .
H14 H 1.0988 0.7028 0.3746 0.017 Uiso 1 1 calc R . .
C15 C 1.0556(6) 0.4198(5) 0.3792(2) 0.0188(8) Uani 1 1 d . . .
C16 C 0.6337(6) 0.1352(5) 0.1583(2) 0.0214(9) Uani 1 1 d . A .
H16A H 0.5166 0.1597 0.1475 0.026 Uiso 1 1 calc R . .
H16B H 0.5962 0.0313 0.1687 0.026 Uiso 1 1 calc R . .
C17 C 0.7107(6) 0.1427(4) 0.0853(2) 0.0192(8) Uani 1 1 d . . .
C19 C 0.8391(11) 0.1491(8) -0.0189(5) 0.0547(19) Uani 1 1 d . . .
C18A C 0.851(3) 0.112(2) 0.0672(9) 0.024(3) Uani 0.648(13) 1 d P A 1
C20A C 0.6972(13) 0.1819(8) -0.0376(5) 0.027(2) Uani 0.648(13) 1 d P A 1
O5A O 0.6038(11) 0.1848(7) 0.0228(4) 0.0201(17) Uani 0.648(13) 1 d P A 1
C18B C 0.680(3) 0.189(2) 0.0092(15) 0.030(4) Uani 0.352(13) 1 d P A 2
C20B C 0.942(3) 0.1324(17) 0.0202(11) 0.045(5) Uani 0.352(13) 1 d P A 2
O5B O 0.894(3) 0.106(3) 0.0905(12) 0.030(4) Uani 0.352(13) 1 d P A 2
Cl1 Cl 0.71549(14) 0.69843(11) 0.11760(6) 0.0216(3) Uani 1 1 d . . .
H3A H 1.222(7) 0.468(6) 0.481(3) 0.034(14) Uiso 1 1 d . . .
H4A H 0.829(6) 0.208(5) 0.271(3) 0.017(11) Uiso 1 1 d . . .
H5A H 1.238(10) 0.924(8) 0.227(4) 0.07(2) Uiso 1 1 d . . .
N1 N 0.7743(5) 0.2387(4) 0.2302(2) 0.0192(7) Uani 1 1 d . . .
N2 N 1.1433(5) 0.9629(4) 0.2235(2) 0.0225(8) Uani 1 1 d . . .
N3 N 0.6808(5) 0.6255(4) 0.4519(2) 0.0182(7) Uani 1 1 d . . .
N4 N 0.6336(5) 0.8266(4) 0.40758(19) 0.0174(7) Uani 1 1 d . . .
N5 N 0.3424(5) 0.5358(4) 0.2239(2) 0.0171(7) Uani 1 1 d . . .
N6 N 0.4837(5) 0.4370(4) 0.3308(2) 0.0189(7) Uani 1 1 d . . .
O1 O 0.8545(4) 0.9603(3) 0.26945(17) 0.0194(6) Uani 1 1 d . . .
O2 O 1.1365(4) 0.9597(3) 0.37030(17) 0.0241(7) Uani 1 1 d . . .
O3 O 1.1748(4) 0.5205(3) 0.44359(17) 0.0212(6) Uani 1 1 d . . .
O4 O 1.0259(4) 0.2836(3) 0.37394(17) 0.0252(7) Uani 1 1 d . . .
O6 O 0.3876(4) 0.7886(3) 0.23346(17) 0.0208(6) Uani 1 1 d . . .
O7 O 0.2979(4) 0.2837(3) 0.21147(17) 0.0220(6) Uani 1 1 d . . .
S1 S 1.01807(14) 0.91268(10) 0.28857(6) 0.0162(3) Uani 1 1 d . . .
H5B H 1.174(9) 1.062(8) 0.222(4) 0.057(18) Uiso 1 1 d . . .
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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N6 C1 H1A 109.5 . .
N6 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
N6 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N5 C2 H2A 109.5 . .
N5 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N5 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
O7 C3 N6 121.2(4) . .
O7 C3 N5 120.9(4) . .
N6 C3 N5 117.9(4) . .
N3 C4 N6 126.2(4) . .
N3 C4 C5 111.6(4) . .
N6 C4 C5 122.2(4) . .
C4 C5 N4 105.1(3) . .
C4 C5 C6 122.5(4) . .
N4 C5 C6 132.4(4) . .
O6 C6 N5 120.5(4) . .
O6 C6 C5 127.3(4) . .
N5 C6 C5 112.2(3) . .
N4 C7 N3 113.3(4) . .
N4 C7 H7 123.4 . .
N3 C7 H7 123.4 . .
N4 C8 H8A 109.5 . .
N4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C14 C9 C10 117.5(4) . .
C14 C9 S1 118.2(3) . .
C10 C9 S1 124.2(3) . .
C11 C10 C9 121.3(4) . .
C11 C10 Cl1 117.7(3) . .
C9 C10 Cl1 121.0(3) . .
C10 C11 C12 121.3(4) . .
C10 C11 H11 119.4 . .
C12 C11 H11 119.4 . .
N1 C12 C11 121.0(4) . .
N1 C12 C13 120.8(4) . .
C11 C12 C13 118.2(3) . .
C14 C13 C12 119.0(3) . .
C14 C13 C15 118.5(4) . .
C12 C13 C15 122.5(3) . .
C9 C14 C13 122.6(4) . .
C9 C14 H14 118.7 . .
C13 C14 H14 118.7 . .
O4 C15 O3 121.8(4) . .
O4 C15 C13 123.1(4) . .
O3 C15 C13 115.1(3) . .
N1 C16 C17 113.3(3) . .
N1 C16 H16A 108.9 . .
C17 C16 H16A 108.9 . .
N1 C16 H16B 108.9 . .
C17 C16 H16B 108.9 . .
H16A C16 H16B 107.7 . .
C18A C17 O5A 112.8(7) . .
C18A C17 C18B 86.3(11) . .
O5A C17 C18B 27.1(7) . .
C18A C17 C16 133.4(7) . .
O5A C17 C16 113.8(4) . .
C18B C17 C16 140.2(10) . .
C18A C17 O5B 17.2(11) . .
O5A C17 O5B 129.7(8) . .
C18B C17 O5B 102.9(12) . .
C16 C17 O5B 116.5(8) . .
C20B C19 C20A 153.5(14) . .
C20B C19 C18B 120.2(16) . .
C20A C19 C18B 33.4(9) . .
C20B C19 C18A 48.4(14) . .
C20A C19 C18A 106.6(8) . .
C18B C19 C18A 73.9(11) . .
C17 C18A C19 102.7(8) . .
C19 C20A O5A 113.8(7) . .
C20A O5A C17 104.0(6) . .
C17 C18B C19 97.0(12) . .
C19 C20B O5B 112.2(19) . .
C20B O5B C17 105.1(13) . .
C12 N1 C16 124.5(3) . .
C12 N1 H4A 112(3) . .
C16 N1 H4A 124(3) . .
S1 N2 H5A 112(4) . .
S1 N2 H5B 111(4) . .
H5A N2 H5B 119(6) . .
C7 N3 C4 103.5(3) . .
C7 N4 C5 106.6(3) . .
C7 N4 C8 125.7(3) . .
C5 N4 C8 127.6(3) . .
C3 N5 C6 126.0(3) . .
C3 N5 C2 115.7(3) . .
C6 N5 C2 118.3(3) . .
C3 N6 C4 119.2(3) . .
C3 N6 C1 119.1(3) . .
C4 N6 C1 121.6(3) . .
C15 O3 H3A 108(3) . .
O2 S1 O1 116.68(17) . .
O2 S1 N2 112.93(19) . .
O1 S1 N2 107.18(19) . .
O2 S1 C9 105.81(18) . .
O1 S1 C9 111.13(18) . .
N2 S1 C9 102.19(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N6 1.462(5) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 N5 1.459(5) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 O7 1.225(5) .
C3 N6 1.364(5) .
C3 N5 1.388(5) .
C4 N3 1.358(5) .
C4 N6 1.364(5) .
C4 C5 1.364(5) .
C5 N4 1.382(5) .
C5 C6 1.410(6) .
C6 O6 1.222(5) .
C6 N5 1.404(5) .
C7 N4 1.325(5) .
C7 N3 1.338(5) .
C7 H7 0.9300 .
C8 N4 1.456(5) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 C14 1.369(5) .
C9 C10 1.413(6) .
C9 S1 1.746(4) .
C10 C11 1.364(5) .
C10 Cl1 1.728(4) .
C11 C12 1.405(5) .
C11 H11 0.9300 .
C12 N1 1.346(5) .
C12 C13 1.409(6) .
C13 C14 1.403(5) .
C13 C15 1.470(6) .
C14 H14 0.9300 .
C15 O4 1.221(5) .
C15 O3 1.315(5) .
C16 N1 1.452(5) .
C16 C17 1.488(6) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18A 1.273(18) .
C17 O5A 1.376(8) .
C17 C18B 1.42(2) .
C17 O5B 1.52(2) .
C19 C20B 0.981(19) .
C19 C20A 1.199(12) .
C19 C18B 1.52(2) .
C19 C18A 1.543(16) .
C20A O5A 1.375(10) .
C20B O5B 1.36(3) .
N1 H4A 0.86(5) .
N2 S1 1.613(3) .
N2 H5A 0.90(8) .
N2 H5B 0.88(7) .
O1 S1 1.434(3) .
O2 S1 1.430(3) .
O3 H3A 0.93(5) .
