#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/87/4078787.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_4078787
loop_
_publ_author_name
'Hudej, Rosana'
'Kljun, Jakob'
'Kandioller, Wolfgang'
'Repnik, Urška'
'Turk, Boris'
'Hartinger, Christian G.'
'Keppler, Bernhard K.'
'Miklavčič, Damijan'
'Turel, Iztok'
_publ_section_title
;
 Synthesis and Biological Evaluation of the Thionated Antibacterial Agent
 Nalidixic Acid and Its Organoruthenium(II) Complex
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              5867
_journal_paper_doi               10.1021/om300424w
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C12 H12 N2 O2 S'
_chemical_formula_sum            'C12 H12 N2 O2 S'
_chemical_formula_weight         248.30
_chemical_name_common            'thionalidixic acid'
_chemical_name_systematic
;
1-Ehyl-7-methyl-4-thioxo-1,4-dihydro-1,8-naphtyridine-3-carboxylic acid
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.309(2)
_cell_angle_beta                 90.376(2)
_cell_angle_gamma                111.183(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6028(3)
_cell_length_b                   8.6374(3)
_cell_length_c                   10.0720(2)
_cell_measurement_reflns_used    2442
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      0.41
_cell_volume                     591.00(4)
_computing_cell_refinement       'DENZO-SMN (Otwinovski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinovski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'π and ω 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  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0266
_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       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4731
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0718P)²+0.1297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                2241
_reflns_number_total             2618
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om300424w_si_001.cif
_cod_data_source_block           k1827
_cod_depositor_comments
'Adding full bibliography for 4078787--4078790.cif.'
_cod_original_cell_volume        591.00(3)
_cod_database_code               4078787
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
S1 S 0.78617(7) 0.40903(6) 1.19083(4) 0.05810(19) Uani 1 1 d .
N2 N 0.49885(18) 0.30475(17) 0.69419(13) 0.0465(3) Uani 1 1 d .
N3 N 0.70605(17) 0.58077(15) 0.81384(12) 0.0412(3) Uani 1 1 d .
O4 O 1.0322(2) 0.7699(2) 1.27178(14) 0.0752(4) Uani 1 1 d .
H4 H 0.9674 0.6701 1.2705 0.113 Uiso 1 1 calc R
O5 O 1.0650(3) 0.93837(19) 1.14007(18) 0.0943(6) Uani 1 1 d .
C6 C 0.8214(2) 0.6917(2) 0.92570(15) 0.0448(3) Uani 1 1 d .
H6 H 0.8849 0.8055 0.9241 0.054 Uiso 1 1 calc R
C7 C 0.6104(2) 0.40955(18) 0.81155(15) 0.0394(3) Uani 1 1 d .
C8 C 0.6352(2) 0.35838(19) 0.92921(15) 0.0422(3) Uani 1 1 d .
C9 C 0.7601(2) 0.47846(19) 1.05181(14) 0.0410(3) Uani 1 1 d .
C10 C 0.6853(2) 0.6388(2) 0.69027(16) 0.0512(4) Uani 1 1 d .
H10A H 0.7162 0.7629 0.7190 0.061 Uiso 1 1 calc R
H10B H 0.5543 0.5827 0.6487 0.061 Uiso 1 1 calc R
C11 C 0.8532(2) 0.64906(19) 1.04466(15) 0.0430(3) Uani 1 1 d .
C12 C 0.5304(3) 0.1836(2) 0.9190(2) 0.0627(5) Uani 1 1 d .
H12 H 0.5390 0.1408 0.9933 0.075 Uiso 1 1 calc R
C13 C 0.2775(3) 0.0251(3) 0.5574(2) 0.0746(6) Uani 1 1 d .
H13A H 0.1481 0.0101 0.5705 0.112 Uiso 1 1 calc R
H13B H 0.2893 -0.0857 0.5344 0.112 Uiso 1 1 calc R
H13C H 0.3147 0.0769 0.4835 0.112 Uiso 1 1 calc R
C14 C 0.8122(3) 0.5972(3) 0.5841(2) 0.0765(6) Uani 1 1 d .
H14A H 0.9424 0.6569 0.6236 0.115 Uiso 1 1 calc R
H14B H 0.7924 0.6337 0.5050 0.115 Uiso 1 1 calc R
H14C H 0.7827 0.4746 0.5560 0.115 Uiso 1 1 calc R
C15 C 0.9911(3) 0.7971(2) 1.15537(18) 0.0574(4) Uani 1 1 d .
C16 C 0.4036(2) 0.1407(2) 0.68867(19) 0.0552(4) Uani 1 1 d .
C17 C 0.4163(3) 0.0767(2) 0.8006(2) 0.0709(6) Uani 1 1 d .
H17 H 0.3467 -0.0389 0.7943 0.085 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 N2 C7 117.84(14)
C6 N3 C7 119.58(12)
C6 N3 C10 120.08(12)
C7 N3 C10 120.30(12)
N3 C6 C11 124.34(14)
N2 C7 N3 116.11(13)
N2 C7 C8 125.01(14)
N3 C7 C8 118.88(13)
C7 C8 C12 115.15(14)
C7 C8 C9 121.95(13)
C12 C8 C9 122.90(14)
C11 C9 C8 115.41(12)
C11 C9 S1 124.64(11)
C8 C9 S1 119.96(11)
N3 C10 C14 111.87(14)
C6 C11 C9 119.83(13)
C6 C11 C15 113.88(14)
C9 C11 C15 126.29(14)
C17 C12 C8 120.19(17)
O5 C15 O4 119.50(16)
O5 C15 C11 121.84(16)
O4 C15 C11 118.66(16)
N2 C16 C17 121.80(15)
N2 C16 C13 117.37(17)
C17 C16 C13 120.82(17)
C12 C17 C16 119.99(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.6986(15)
N2 C16 1.324(2)
N2 C7 1.3426(19)
N3 C6 1.3290(19)
N3 C7 1.3860(18)
N3 C10 1.4864(18)
O4 C15 1.312(2)
O5 C15 1.197(2)
C6 C11 1.387(2)
C7 C8 1.403(2)
C8 C12 1.404(2)
C8 C9 1.449(2)
C9 C11 1.407(2)
C10 C14 1.504(3)
C11 C15 1.497(2)
C12 C17 1.362(3)
C13 C16 1.503(2)
C16 C17 1.397(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659845
