#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/87/4078790.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_4078790
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         'C14 H16 N2 O3'
_chemical_formula_sum            'C14 H16 N2 O3'
_chemical_formula_weight         260.29
_chemical_name_common            'nalidixic acid ethyl ester'
_chemical_name_systematic
;
ethyl 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.485(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6074(3)
_cell_length_b                   13.4742(6)
_cell_length_c                   20.3128(10)
_cell_measurement_reflns_used    3852
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.2694
_cell_measurement_theta_min      3.0175
_cell_volume                     1252.97(12)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9260
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0648P)²+0.5588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                2201
_reflns_number_total             2746
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om300424w_si_001.cif
_cod_data_source_block           mo155
_cod_depositor_comments
'Adding full bibliography for 4078787--4078790.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4078790
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_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
O17 O 0.0190(3) 0.13220(8) 0.85813(5) 0.0261(3) Uani 1 1 d .
O15 O 0.1246(3) -0.03020(9) 0.85733(6) 0.0354(3) Uani 1 1 d .
O14 O 0.3440(3) 0.25229(8) 0.78669(6) 0.0273(3) Uani 1 1 d .
N8 N 0.8412(3) 0.08361(9) 0.62501(6) 0.0195(3) Uani 1 1 d .
N1 N 0.5658(3) -0.00421(9) 0.69449(6) 0.0183(3) Uani 1 1 d .
C3 C 0.3183(3) 0.07475(11) 0.77903(7) 0.0190(3) Uani 1 1 d .
C10 C 0.5926(3) 0.17390(11) 0.70560(7) 0.0184(3) Uani 1 1 d .
C12 C 0.6244(4) -0.09669(11) 0.65869(8) 0.0230(3) Uani 1 1 d .
H12A H 0.5769 -0.1546 0.6855 0.028 Uiso 1 1 calc R
H12B H 0.8350 -0.1000 0.6532 0.028 Uiso 1 1 calc R
C9 C 0.6702(3) 0.08671(11) 0.67447(7) 0.0177(3) Uani 1 1 d .
C4 C 0.4073(3) 0.17373(11) 0.76046(7) 0.0191(3) Uani 1 1 d .
C7 C 0.9427(3) 0.16964(11) 0.60444(7) 0.0208(3) Uani 1 1 d .
C2 C 0.4004(3) -0.00690(11) 0.74498(7) 0.0193(3) Uani 1 1 d .
H2 H 0.3354 -0.0700 0.7581 0.023 Uiso 1 1 calc R
C11 C 1.1300(4) 0.16450(12) 0.54851(8) 0.0257(4) Uani 1 1 d .
H11A H 1.1508 0.0952 0.5353 0.039 Uiso 1 1 calc R
H11B H 1.3232 0.1923 0.5631 0.039 Uiso 1 1 calc R
H11C H 1.0381 0.2027 0.5107 0.039 Uiso 1 1 calc R
C16 C 0.1473(3) 0.05260(11) 0.83481(7) 0.0219(3) Uani 1 1 d .
C5 C 0.7004(3) 0.26285(11) 0.68231(8) 0.0222(3) Uani 1 1 d .
H5 H 0.6516 0.3243 0.7012 0.027 Uiso 1 1 calc R
C6 C 0.8767(3) 0.26115(12) 0.63219(8) 0.0233(3) Uani 1 1 d .
H6 H 0.9529 0.3211 0.6165 0.028 Uiso 1 1 calc R
C13 C 0.4479(4) -0.10239(13) 0.59122(8) 0.0300(4) Uani 1 1 d .
H13A H 0.2402 -0.0941 0.5961 0.045 Uiso 1 1 calc R
H13B H 0.4788 -0.1671 0.5711 0.045 Uiso 1 1 calc R
H13C H 0.5106 -0.0497 0.5627 0.045 Uiso 1 1 calc R
C18 C -0.1431(4) 0.11528(13) 0.91453(8) 0.0307(4) Uani 1 1 d .
H18A H -0.2376 0.0492 0.9106 0.037 Uiso 1 1 calc R
H18B H -0.2980 0.1661 0.9152 0.037 Uiso 1 1 calc R
C19 C 0.0608(4) 0.12046(14) 0.97800(9) 0.0359(4) Uani 1 1 d .
H19A H 0.2090 0.0683 0.9780 0.054 Uiso 1 1 calc R
H19B H -0.0507 0.1110 1.0158 0.054 Uiso 1 1 calc R
H19C H 0.1565 0.1855 0.9814 0.054 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 O17 C18 116.12(12)
C7 N8 C9 117.53(13)
C2 N1 C9 119.34(12)
C2 N1 C12 120.10(12)
C9 N1 C12 120.50(12)
C2 C3 C4 120.02(13)
C2 C3 C16 115.07(13)
C4 C3 C16 124.88(13)
C9 C10 C5 116.58(14)
C9 C10 C4 122.55(13)
C5 C10 C4 120.87(13)
N1 C12 C13 112.18(13)
N8 C9 N1 116.17(13)
N8 C9 C10 124.36(13)
N1 C9 C10 119.46(13)
O14 C4 C3 125.84(14)
O14 C4 C10 120.58(13)
C3 C4 C10 113.58(13)
N8 C7 C6 122.53(14)
N8 C7 C11 116.60(14)
C6 C7 C11 120.85(14)
N1 C2 C3 125.00(14)
O15 C16 O17 122.89(14)
O15 C16 C3 123.30(14)
O17 C16 C3 113.82(13)
C6 C5 C10 119.91(14)
C5 C6 C7 119.08(14)
O17 C18 C19 109.89(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O17 C16 1.3370(19)
O17 C18 1.4546(19)
O15 C16 1.2148(19)
O14 C4 1.2349(18)
N8 C7 1.3347(19)
N8 C9 1.3455(19)
N1 C2 1.3454(19)
N1 C9 1.3936(18)
N1 C12 1.4829(18)
C3 C2 1.375(2)
C3 C4 1.457(2)
C3 C16 1.482(2)
C10 C9 1.400(2)
C10 C5 1.400(2)
C10 C4 1.478(2)
C12 C13 1.514(2)
C7 C6 1.403(2)
C7 C11 1.504(2)
C5 C6 1.372(2)
C18 C19 1.509(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 105876
