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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/64/1516413.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_1516413
loop_
_publ_author_name
'Santos, Rui C.'
'Figueira, Rita M. B. B. M.'
'Piedade, M Fátima M'
'Diogo, Hermínio P'
'Minas da Piedade, Manuel E.'
_publ_section_title
;
 Energetics and structure of hydroxynicotinic acids. Crystal structures of
 2-, 4-, 6-hydroxynicotinic and 5-chloro-6-hydroxynicotinic acids.
;
_journal_issue                   43
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              14291
_journal_page_last               14309
_journal_paper_doi               10.1021/jp906908n
_journal_volume                  113
_journal_year                    2009
_chemical_formula_sum            'C6 H5 N O3'
_chemical_formula_weight         139.11
_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                 90.007(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.7970(10)
_cell_length_b                   7.354(2)
_cell_length_c                   20.905(4)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      16.4
_cell_volume                     583.7(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.690
_diffrn_measured_fraction_theta_max 0.690
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            792
_diffrn_reflns_theta_full        71.82
_diffrn_reflns_theta_max         71.82
_diffrn_reflns_theta_min         4.23
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.063(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1094P)²+0.1081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                656
_reflns_number_total             792
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jp906908n_si_002.cif
_cod_data_source_block           new
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1516413
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
O3 O -0.2360(5) 0.4542(2) 0.33045(8) 0.0520(7) Uani 1 1 d
O1 O 0.2837(5) 0.1906(2) 0.47681(8) 0.0507(7) Uani 1 1 d
O2 O -0.0182(5) 0.4699(2) 0.42866(9) 0.0526(7) Uani 1 1 d
N1 N 0.3367(5) -0.0648(2) 0.41631(9) 0.0351(6) Uani 1 1 d
C2 C 0.0505(5) 0.1920(3) 0.37025(9) 0.0304(6) Uani 1 1 d
C3 C 0.0085(5) 0.0916(3) 0.31454(11) 0.0335(7) Uani 1 1 d
C6 C -0.0802(5) 0.3810(3) 0.37438(10) 0.0363(7) Uani 1 1 d
C4 C 0.1312(6) -0.0853(3) 0.30953(12) 0.0375(7) Uani 1 1 d
C1 C 0.2271(6) 0.1102(3) 0.42409(10) 0.0340(6) Uani 1 1 d
C5 C 0.2945(6) -0.1619(3) 0.36128(11) 0.0367(7) Uani 1 1 d
H5 H 0.386(8) -0.289(4) 0.3632(13) 0.056(8) Uiso 1 1 d
H3 H -0.113(7) 0.146(3) 0.2790(12) 0.045(6) Uiso 1 1 d
H4 H 0.099(7) -0.157(3) 0.2731(12) 0.042(6) Uiso 1 1 d
H2 H 0.098(12) 0.383(5) 0.454(2) 0.098(12) Uiso 1 1 d
H1N H 0.460(8) -0.114(4) 0.4529(14) 0.053(7) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0558(12) 0.0465(12) 0.0537(13) 0.0033(7) -0.0139(8) 0.0132(7)
O1 0.0693(13) 0.0457(12) 0.0373(12) -0.0037(7) -0.0126(8) 0.0147(7)
O2 0.0720(13) 0.0416(12) 0.0442(13) -0.0046(8) -0.0068(8) 0.0146(8)
N1 0.0342(11) 0.0339(12) 0.0372(13) 0.0040(8) -0.0006(7) 0.0035(7)
C2 0.0229(13) 0.0347(14) 0.0337(14) 0.0023(8) 0.0018(7) -0.0001(7)
C3 0.0239(13) 0.0419(15) 0.0346(14) 0.0031(8) -0.0013(8) 0.0002(7)
C6 0.0307(14) 0.0398(14) 0.0384(15) 0.0029(9) -0.0012(9) 0.0028(8)
C4 0.0313(14) 0.0412(15) 0.0398(15) -0.0081(10) -0.0006(9) -0.0013(8)
C1 0.0328(13) 0.0355(14) 0.0336(15) 0.0012(9) 0.0004(8) -0.0002(8)
C5 0.0291(13) 0.0360(15) 0.0451(15) -0.0013(9) 0.0037(8) -0.0008(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C6 O2 H2 103(2)
C5 N1 C1 124.01(18)
C5 N1 H1N 122.1(17)
C1 N1 H1N 113.8(17)
C3 C2 C1 119.14(19)
C3 C2 C6 120.68(18)
C1 C2 C6 120.18(19)
C2 C3 C4 121.6(2)
C2 C3 H3 119.0(15)
C4 C3 H3 119.4(15)
O3 C6 O2 120.76(19)
O3 C6 C2 122.3(2)
O2 C6 C2 116.92(18)
C5 C4 C3 118.6(2)
C5 C4 H4 118.1(15)
C3 C4 H4 123.3(15)
O1 C1 N1 119.47(18)
O1 C1 C2 124.2(2)
N1 C1 C2 116.29(19)
N1 C5 C4 120.3(2)
N1 C5 H5 114.5(15)
C4 C5 H5 125.1(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C6 1.218(2)
O1 C1 1.269(3)
O2 C6 1.331(3)
O2 H2 0.94(4)
N1 C5 1.363(3)
N1 C1 1.363(3)
N1 H1N 0.97(3)
C2 C3 1.388(3)
C2 C1 1.441(3)
C2 C6 1.478(3)
C3 C4 1.386(3)
C3 H3 0.96(3)
C4 C5 1.368(3)
C4 H4 0.94(3)
C5 H5 1.00(3)
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
C1 C2 C3 C4 0.2(3)
C6 C2 C3 C4 179.57(18)
C3 C2 C6 O3 1.9(3)
C1 C2 C6 O3 -178.7(2)
C3 C2 C6 O2 -177.64(19)
C1 C2 C6 O2 1.7(3)
C2 C3 C4 C5 0.6(3)
C5 N1 C1 O1 -178.75(19)
C5 N1 C1 C2 1.3(3)
C3 C2 C1 O1 178.95(19)
C6 C2 C1 O1 -0.4(3)
C3 C2 C1 N1 -1.1(3)
C6 C2 C1 N1 179.54(17)
C1 N1 C5 C4 -0.6(3)
C3 C4 C5 N1 -0.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 69114
