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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/68/4506810.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_4506810
loop_
_publ_author_name
'Gangavaram, Swarupa'
'Raghavender, S.'
'Sanphui, Palash'
'Pal, Sharmistha'
'Manjunatha, Sulur G.'
'Nambiar, Sudhir'
'Nangia, Ashwini'
_publ_section_title
;
 Polymorphs and Cocrystals of Nalidixic Acid
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4963
_journal_paper_doi               10.1021/cg300895c
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C15 H15 N2 O4'
_chemical_formula_weight         287.29
_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                87.82(3)
_cell_angle_beta                 87.78(4)
_cell_angle_gamma                67.56(4)
_cell_formula_units_Z            2
_cell_length_a                   7.559(4)
_cell_length_b                   9.765(4)
_cell_length_c                   10.036(4)
_cell_measurement_reflns_used    772
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.3150
_cell_measurement_theta_min      2.9105
_cell_volume                     684.0(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0813
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4694
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0637
_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)+(0.0436P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                1440
_reflns_number_total             2784
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300895c_si_004.cif
_cod_data_source_block           NA-HYQ
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        684.0(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4506810
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
C4 C 0.2422(3) -0.0853(3) 0.5230(3) 0.0385(7) Uani 1 1 d .
N2 N 0.3903(3) 0.1756(2) 0.2417(2) 0.0428(6) Uani 1 1 d .
O3 O 0.2293(3) -0.3172(2) 0.5903(2) 0.0611(6) Uani 1 1 d .
C10 C 0.3356(3) 0.0981(3) 0.3371(3) 0.0369(6) Uani 1 1 d .
O2 O 0.1219(3) -0.1343(2) 0.7319(2) 0.0633(6) Uani 1 1 d .
H2 H 0.1132 -0.0481 0.7346 0.095 Uiso 1 1 calc R
C5 C 0.2036(4) 0.0631(3) 0.5595(3) 0.0429(7) Uani 1 1 d .
C6 C 0.2538(3) 0.1542(3) 0.4600(3) 0.0388(7) Uani 1 1 d .
O1 O 0.1314(3) 0.1121(2) 0.6715(2) 0.0602(6) Uani 1 1 d .
N1 N 0.3678(3) -0.0488(2) 0.3082(2) 0.0409(6) Uani 1 1 d .
C3 C 0.3206(3) -0.1323(3) 0.4004(3) 0.0429(7) Uani 1 1 d .
H3 H 0.3429 -0.2295 0.3793 0.051 Uiso 1 1 calc R
C9 C 0.3602(4) 0.3160(3) 0.2667(3) 0.0470(8) Uani 1 1 d .
C7 C 0.2228(4) 0.3023(3) 0.4823(3) 0.0512(8) Uani 1 1 d .
H7 H 0.1664 0.3458 0.5621 0.061 Uiso 1 1 calc R
C12 C 0.1981(4) -0.1895(4) 0.6164(3) 0.0476(8) Uani 1 1 d .
C8 C 0.2759(4) 0.3820(3) 0.3862(3) 0.0542(8) Uani 1 1 d .
H8 H 0.2560 0.4804 0.4001 0.065 Uiso 1 1 calc R
C2 C 0.4416(4) -0.1075(3) 0.1756(3) 0.0543(8) Uani 1 1 d .
H2A H 0.5108 -0.2138 0.1835 0.065 Uiso 1 1 calc R
H2B H 0.5306 -0.0638 0.1417 0.065 Uiso 1 1 calc R
C11 C 0.4247(4) 0.4003(3) 0.1606(3) 0.0620(9) Uani 1 1 d .
H11A H 0.5620 0.3646 0.1577 0.093 Uiso 1 1 calc R
H11B H 0.3730 0.5038 0.1804 0.093 Uiso 1 1 calc R
H11C H 0.3804 0.3866 0.0757 0.093 Uiso 1 1 calc R
C1 C 0.2839(5) -0.0751(4) 0.0786(3) 0.0789(11) Uani 1 1 d .
H1A H 0.3377 -0.1119 -0.0073 0.118 Uiso 1 1 calc R
H1B H 0.2137 0.0300 0.0714 0.118 Uiso 1 1 calc R
H1C H 0.1992 -0.1226 0.1094 0.118 Uiso 1 1 calc R
O4 O 0.1957(3) 0.4649(2) 0.75799(19) 0.0575(6) Uani 1 1 d .
H4 H 0.1840 0.5453 0.7238 0.086 Uiso 1 1 calc R
C14 C 0.0333(4) 0.6196(3) 0.9431(3) 0.0448(7) Uani 1 1 d .
H14 H 0.0552 0.7001 0.9050 0.054 Uiso 1 1 calc R
C13 C 0.0954(4) 0.4864(3) 0.8779(3) 0.0423(7) Uani 1 1 d .
C15 C -0.0613(4) 0.6321(3) 1.0649(3) 0.0470(8) Uani 1 1 d .
H15 H -0.1026 0.7214 1.1090 0.056 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 C4 C5 119.7(2) . .
C3 C4 C12 119.4(3) . .
C5 C4 C12 120.9(3) . .
C9 N2 C10 117.3(2) . .
N2 C10 C6 124.3(2) . .
N2 C10 N1 116.2(2) . .
C6 C10 N1 119.5(2) . .
C12 O2 H2 109.5 . .
O1 C5 C4 122.2(2) . .
O1 C5 C6 121.9(3) . .
C4 C5 C6 115.8(2) . .
C10 C6 C7 116.8(2) . .
C10 C6 C5 121.3(2) . .
C7 C6 C5 121.9(3) . .
C3 N1 C10 118.9(2) . .
C3 N1 C2 120.5(2) . .
C10 N1 C2 120.5(2) . .
N1 C3 C4 124.8(3) . .
N1 C3 H3 117.6 . .
C4 C3 H3 117.6 . .
N2 C9 C8 122.2(2) . .
N2 C9 C11 116.8(3) . .
C8 C9 C11 121.0(3) . .
C8 C7 C6 119.4(3) . .
C8 C7 H7 120.3 . .
C6 C7 H7 120.3 . .
O3 C12 O2 121.5(3) . .
O3 C12 C4 123.4(3) . .
O2 C12 C4 115.1(3) . .
C7 C8 C9 120.0(3) . .
C7 C8 H8 120.0 . .
C9 C8 H8 120.0 . .
N1 C2 C1 111.9(2) . .
N1 C2 H2A 109.2 . .
C1 C2 H2A 109.2 . .
N1 C2 H2B 109.2 . .
C1 C2 H2B 109.2 . .
H2A C2 H2B 107.9 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C13 O4 H4 109.5 . .
C15 C14 C13 119.6(2) . .
C15 C14 H14 120.2 . .
C13 C14 H14 120.2 . .
O4 C13 C15 117.6(2) . 2_567
O4 C13 C14 122.7(2) . .
C15 C13 C14 119.7(2) 2_567 .
C14 C15 C13 120.7(2) . 2_567
C14 C15 H15 119.7 . .
C13 C15 H15 119.7 2_567 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C4 C3 1.362(3) .
C4 C5 1.425(4) .
C4 C12 1.479(4) .
N2 C9 1.333(3) .
N2 C10 1.347(3) .
O3 C12 1.215(3) .
C10 C6 1.393(3) .
C10 N1 1.401(3) .
O2 C12 1.313(3) .
O2 H2 0.8200 .
C5 O1 1.259(3) .
C5 C6 1.446(3) .
C6 C7 1.399(3) .
N1 C3 1.337(3) .
N1 C2 1.472(3) .
C3 H3 0.9300 .
C9 C8 1.395(4) .
C9 C11 1.500(3) .
C7 C8 1.359(4) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C2 C1 1.499(4) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
O4 C13 1.376(3) .
O4 H4 0.8200 .
C14 C15 1.377(3) .
C14 C13 1.384(4) .
C14 H14 0.9300 .
C13 C15 1.380(3) 2_567
C15 C13 1.379(3) 2_567
C15 H15 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146223
